Oxalyl chloride → 6831-57-8

HRID 1691775Notes

Reaction equation

HRID 1691775 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=O.C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]([Cl:19])=[O:15]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1383242-Bromo-4,5-dimethoxyphenylacetic acid

Product 1

HCID 51858206831-57-8Yield 103.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-4,5-dimethoxy-phenyl)-acetic acid (833 mg, 3.03 mmol) in dichloromethane (10 mL) were added oxalyl chloride (0.29 mL, 3.33 mmol) and dimethylformamide (1 drop) under argon atmosphere. The mixture was stirred for 3.5 hours at room temperature, then was concentrated to dryness under reduced pressure. Dichloroethane (15 mL) was added, and resulting solution was back evaporated to dryness to obtain crude (2-bromo-4,5-dimethoxy-phenyl)-acetyl chloride (917 mg).

Workup

  1. concentrationwas concentrated to dryness under reduced pressure
  2. additionDichloroethane (15 mL) was added
  3. customresulting solution
  4. customwas back evaporated to dryness

Sources & evidence

ORD record
ord-dd8ba4b4db1e496ca580a8ae41b03ca3
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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