Triphenylphosphine → 2-Chloro-4-(methylsulfanyl)benzaldehyde

HRID 21460Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O.[B-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu+]>[Cl:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[CH:4]=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-chloro-4-(methylsulphenyl)-benzoyl chloride (1.0 g), triphenyl phosphine (2.47 g) and bis(triphenylphosphine)copper (I) borohydride (1.0 g) in acetone was stirred at 0° C. for 1 hour. Further his (triphenylphosphine)copper (I) borohydride (1.5 g) was added and the mixture was stirred for 2 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in chloroform and treated with copper (I) bromide (2.1 g). The filtrate was evaporated to dryness and the residue was purified by chromotography eluted with a mixture of ethyl acetate and hexane to give 2-chloro-4-(methylsulphenyl)benzaldehyde (0.83 g) as an off-white solid, m.p. 76°-77° C.

Workup

stirringthe mixture was stirred for 2 hours
filtrationThe mixture was filtered
customthe filtrate was evaporated to dryness
dissolutionThe residue was dissolved in chloroform
additiontreated with copper (I) bromide (2.1 g)
customThe filtrate was evaporated to dryness
customthe residue was purified by chromotography
washeluted with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-2216a806563e452ca7db02216554b46a
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424276

Reaction notes

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