Oxalyl chloride → 4-(1-Bromoethyl)benzoyl chloride

HRID 468770Notes

Reaction equation

HRID 468770 reaction equation
[Br:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)[CH3:3].C(Cl)(=O)C([Cl:16])=O>C(Cl)Cl.CN(C)C=O>[Br:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([Cl:16])=[O:9])=[CH:6][CH:5]=1)[CH3:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 51462254-(1-Bromoethyl)benzoic acid

Product 1

HCID 866749384-(1-Bromoethyl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(1-bromoethyl)benzoic acid (50.7 mg, 0.221 mmol) in methylene chloride (4.0 mL, 62 mmol) was added 2.0 M of oxalyl chloride in methylene chloride (0.25 mL) followed by 3 drops of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for one hour, and then evaporated in vacuo to remove dichloromethane and excess oxalyl chloride. The crude product was carried forward without purification.

Workup

  1. customevaporated in vacuo
  2. customto remove dichloromethane and excess oxalyl chloride
  3. customThe crude product was carried forward without purification

Sources & evidence

ORD record
ord-e26bede17b544c6bb97375c524c8c330
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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