Oxalyl chloride → 5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbonyl chloride

HRID 1512670Notes

Reaction equation

HRID 1512670 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14]([Cl:20])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chloride2×HCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 866524055-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (4.2 g, 14.89 mmol) was dissolved in CH2Cl2 (42 mL) under N2 atmosphere. Oxalyl chloride (2.6 mL, 29.78 mmol) and DMF (5 drops) were added and the reaction stirred for 2.5 hours at room temperature. Then, additional oxalyl chloride (5 mL, 57.3 mmol) was added. After 30 minutes, the reaction mixture was concentrated and placed under high vacuum. The crude material was used directly in the next step.

Workup

  1. waitAfter 30 minutes
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-8ee5c0a6deeb4b19ba4cfd4dfd012123
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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