Triphenylphosphine Oxide → 2-Chloro-4-fluoro-5-nitrobenzoyl chloride

HRID 2384585Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:17])=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([Cl:17])=[O:5]

Participants

Reactant 3

HCID 13097Triphenylphosphine Oxide

HCID 24386Thionyl Chloride

HCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Product 1

HCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chloride

Procedure

22.3 g (0.1 mol) of 2-chloro-4-fluoro-5-nitrobenzoic acid 16.8 g (0.14 mol) of thionyl chloride 0.1 g (0.00036 mol) of triphenyl phosphine oxide Yield*: 46.5 g (>99% of theory) of the title compound as a solution in chlorobenzene * In these examples, the yield was determined by means of 19F-NMR with internal standard. Fluoride value: 0.01 g/l

Sources & evidence

ORD record: ord-7156f29c93134224b24fc0e863dd64e4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263806B2

Reaction notes

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