83647-40-9
3-BROMO-2-METHYL-BENZALDEHYDE
CAS: 83647-40-9
Molecular Formula: C8H7BrO
83647-40-9 - Names and Identifiers
83647-40-9 - 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 |
83647-40-9 - Upstream Downstream Industry
83647-40-9 - 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
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View History
Raw Materials for 83647-40-9
2,6-Dibromotoluene
3-Bromo-2-methylbenzoic acid
3-bromo-N-methoxy-N,2-dimethylbenzamide
(3-broMo-2-Methylphenyl)Methanol
3-Bromo-2-methylbenzoic acid
3-bromo-N-methoxy-N,2-dimethylbenzamide
(3-broMo-2-Methylphenyl)Methanol
Downstream Products for 83647-40-9