Triphenylphosphine → 2-Nitro-4-(trifluoromethyl)benzaldehyde

HRID 266549Notes

Reaction equation

HRID 266549 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O>[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[CH:9][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 143235242-Nitro-4-(trifluoromethyl)benzoyl chloride

Product 1

HCID 111603052-Nitro-4-(trifluoromethyl)benzaldehydeYield 85.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-nitro-4-trifluoromethylbenzoyl chloride (8.0 g) and triphenylphosphine (16.5 g) in dry acetone (75 ml) was treated with bis-(triphenylphosphine)tetrahydroboratocopper(I) (19.8 g). The resulting suspension was stirred for 1 hour, filtered and washed with diethyl ether. The filtrate was evaporated to dryness and the resulting residue was subjected to chromatography, eluting with a mixture of diethyl ether and n-hexane (1:5 v/v), to give 2-nitro-4-trifluoromethylbenzaldehyde (5.91 g) in the form of an off-white solid, m.p. 63° C.

Workup

  1. filtrationfiltered
  2. washwashed with diethyl ether
  3. customThe filtrate was evaporated to dryness
  4. washeluting with a mixture of diethyl ether and n-hexane (1:5 v/v)

Sources & evidence

ORD record
ord-645f1725a9424f278b6ce2bd0585fecb
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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