Dimethylformamide → 4-Iodobenzoyl chloride

HRID 479532Notes

Reaction equation

HRID 479532 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:14])=O.CN(C)C=O>C(Cl)Cl>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:14])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120854-Iodobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 743734-Iodobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4-iodobenzoic acid (20.0 g, 80.6 mL) in CH2Cl2 (350 mL) at 0° C. was treated with oxalyl chloride (42.3 mL of a 2.0 M solution in CH2Cl2, 81.7 mmol). Dimethylformamide was added (0.5 mL) until a homogeneous solution was achieved and then the cooling bath was removed. The reaction mixture was stirred at ambient temperature for 3 hours and then concentrated to provide crude 4iodobenzoyl chloride as a waxy oil that was used without further purification.

Workup

  1. customthe cooling bath was removed
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-90afd7de93734704b093f9142776b213
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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