Oxalyl chloride → 3-Fluoro-5-methoxybenzoyl chloride

HRID 238007Notes

Reaction equation

HRID 238007 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C([Cl:16])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5]([Cl:16])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 219424693-Fluoro-5-methoxybenzoic acid

Product 1

HCID 866170143-Fluoro-5-methoxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

3-fluoro-5-methoxybenzoic acid (5 g, 0.029 mol) was stirred in CH2Cl2 (50 ml) at 0° C. under an argon atmosphere. DMF (9 drops, catalytic) was added, followed by oxalyl chloride (12.7 ml, 0.147 mol). Reaction was warmed to room temperature then stirred under argon for one hour. Reaction was concentrated in vacuo to yield 3-fluoro-5-methoxybenzoyl chloride (BA67).

Workup

  1. customReaction
  2. customReaction
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-81bed34386834e2b92b6b3f50f89cbd0
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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