Oxalyl chloride → 4-Bromo-2-fluoro-benzoic acid methyl ester

HRID 55851Notes

Reaction equation

HRID 55851 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.[C:12](Cl)(=O)C(Cl)=O>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl esterYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-bromo-2-fluorobenzoic acid (4 g, 18 mmol) in methanol (10 mL) was added dropwise oxalyl dichloride (4.6 g, 36 mmol). The reaction was heated to 60° C. overnight and added slowly into ice water, and extracted with DCM (50 mL×2). The combined extracts were washed with brine, dried over Na2SO4 and concentrated to give the desired product (3.7 g, 88%) as brown solid.

Workup

  1. extractionextracted with DCM (50 mL×2)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-10c82725120c437a89cc7858c5bd9754
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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