4-Fluoro-3-phenoxybenzaldehyde → HCID 23502104, compound

HRID 1835037Notes

Reaction equation

HRID 1835037 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1([Li])C=CC=CC=1.[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][C:33]=1[O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CCOCC.[Cl-].[NH4+]>[F:31][C:32]1[CH:39]=[CH:38][C:35](/[CH:36]=[CH:2]/[O:3][CH3:4])=[CH:34][C:33]=1[O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178506676HCID 178506676, compound

Product 1

HCID 23502104HCID 23502104, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred suspension of (methoxymethyl)triphenylphosphonium chloride (2.48 g) in ether (50 ml) at room temperature under nitrogen is added phenyllithium (4 ml of a 1.8 M solution in ether, 7.2 mmol) and the resulting mixture stirred for 20 minutes. 4-fluoro-3-phenoxybenzaldehyde (1.30 g, 6.0 mmol) is then added and the reaction is stirred for 4 hours. The reaction mixture was diluted with saturated aqueous ammonium chloride (20 ml) and diethyl ether (50 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel eluting with ether:hexane (5:95) to afford the title compound as a colorless liquid (1.30 g, 89%) which is characterized by 1HNMR, IR and mass spectral analyses.

Workup

  1. stirringthe reaction is stirred for 4 hours
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed on silica gel eluting with ether:hexane (5:95)

Sources & evidence

ORD record
ord-575ec535b637497abc921027d05021e0
Source dataset
uspto-grants-2004_08
Patent number
US06770463B2

Reaction notes

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