Oxalyl chloride → 5-Bromofuran-2-carbonyl chloride

HRID 2280322Notes

Reaction equation

HRID 2280322 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:13])=O>C(Cl)Cl>[Br:1][C:2]1[O:6][C:5]([C:7]([Cl:13])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 27570115-Bromofuran-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., to a stirred solution of 5-bromofuran-2-carboxylic acid (3.00 g, 15.7 mmol) in DCM (30 mL) was added dropwise oxalyl dichloride (4.50 mL, 47.1 mmol). Then the resulted mixture was stirred at room temperature for 2 h. TLC and LC-MS showed no starting material. The volatile was removed under reduced pressure and the residual yellow solid was used without further purification (3.20 g, quant.)

Workup

  1. customThe volatile was removed under reduced pressure
  2. customthe residual yellow solid was used without further purification (3.20 g, quant.)

Sources & evidence

ORD record
ord-5a7c57e6d15340b89193ca881af20a0b
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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