Dimethylformamide → 5-Bromo-3-formyl-4-methoxybenzoyl chloride

HRID 1752874Notes

Reaction equation

HRID 1752874 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:11]=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C([Cl:18])=O.CN(C)C=O>O1CCCC1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:11]=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([Cl:18])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 866076935-Bromo-3-formyl-4-methoxybenzoic acid

Product 1

HCID 866076925-Bromo-3-formyl-4-methoxybenzoyl chlorideYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-3-formyl-4-methoxybenzoic acid (480 mg, 1.84 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) and the solution was flushed with dry nitrogen for 5 minutes. Oxalyl chloride (1.2 mL, 2.4 mmol, 1.3 eq) was added slowly to the solution while vigorous stirring and then a catalytic amount of dry dimethylformamide was added. The mixture was stirred for 1 hour and then concentrated by rotary evaporation and dried on high vacuum to give 5-bromo-3-formyl-4-methoxybenzoyl chloride (501 mg) as yellow crystals.

Workup

  1. customthe solution was flushed with dry nitrogen for 5 minutes
  2. stirringThe mixture was stirred for 1 hour
  3. concentrationconcentrated by rotary evaporation
  4. customdried on high vacuum

Sources & evidence

ORD record
ord-de5d405d606c441a9d950a811a7d3a05
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

Loading…