3-Bromo-o-tolualdehyde, 2-Bromo-6-formyltoluene

3-Bromo-o-tolualdehyde, 2-Bromo-6-formyltoluene - Names and Identifiers

Name	3-BROMO-2-METHYL-BENZALDEHYDE
Synonyms	3-broMo-2-tolualdehyde 3-BROMO-2-METHYL-BENZALDEHYDE Benzaldehyde, 3-bromo-2-methyl- 3-Bromo-o-tolualdehyde, 2-Bromo-6-formyltoluene
CAS	83647-40-9
EINECS	200-258-5

3-Bromo-o-tolualdehyde, 2-Bromo-6-formyltoluene - Physico-chemical Properties

Molecular Formula	C8H7BrO
Molar Mass	199.04458
Density	1.490±0.06 g/cm3(Predicted)
Boling Point	255.3±20.0 °C(Predicted)
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C

3-Bromo-o-tolualdehyde, 2-Bromo-6-formyltoluene - Upstream Downstream Industry

Raw Materials	2,6-Dibromotoluene 3-Bromo-2-methylbenzoic acid 3-bromo-N-methoxy-N,2-dimethylbenzamide (3-broMo-2-Methylphenyl)Methanol
Downstream Products	5-BROMO-2-METHYLBENZALDEHYDE 5-bromo-4-methyl-1H-indole-2-carboxylic acid

3-Bromo-o-tolualdehyde, 2-Bromo-6-formyltoluene - Uses and synthesis methods

overview

3-Bromo-2-methylbenzaldehyde can be used as an intermediate in pharmaceutical synthesis. It can be reduced from 3-bromo-2-methylbenzoic acid as a starting material to obtain (3-bromo-2-methylphenyl) Methanol, and then oxidized to prepare 3-bromo-2-methylbenzaldehyde.

Preparation

Step 1: Add 3-bromo-2-methylbenzoic acid (3.00g,14.0mmol) to a suspension of sodium borohydride (0.630g,16.7mmol) in THF(82mL). Stir the mixture until the gas escape stops, and then add iodine (1.77g,6.98mmol) in small parts. The mixture was stirred at room temperature for 2 hours, and then the reaction was carefully quenched by slow addition of HCl aqueous solution (2N). The resulting mixture was diluted with water and extracted with ether. The organic layer was washed three times with NaOH aqueous solution (2N), once with brine, dried by magnesium sulfate, filtered and concentrated to obtain a white solid (3-bromo-2-methylphenyl) methanol (2.79g).

Step 2: Slowly add oxalyl chloride (2.0M in dichloromethane, 10.4mL,20.8mmol) to a solution of dichloromethane (55mL) cooled to -78°C under nitrogen. The mixture was stirred at -78°C for 30 minutes, and then (3-bromo-2-methylphenyl) methanol (2.79g,13.9mmol) solution of dichloromethane (15mL) was added dropwise through the casing. Stir the mixture for 1 hour, slowly add triethylamine (5.8mL,41.8mmol), and raise the temperature of the reactant to room temperature. The mixture was washed with saturated sodium bicarbonate aqueous solution, water and brine. The organic layer was dried by magnesium sulfate, filtered and concentrated to obtain 3-bromo-2-methylbenzaldehyde (2.76g).

Last Update：2024-04-10 22:41:03