3-Bromobenzaldehyde → 1-(3-Bromophenyl)-7-chloro-1-hepten-3-one

HRID 67884Notes

Reaction equation

HRID 67884 reaction equation
[Cl-:1].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=O>C1(C)C(C)=CC=CC=1>[Br:28][C:29]1[CH:30]=[C:31]([CH:32]=[CH:8][C:3](=[O:2])[CH2:4][CH2:5][CH2:6][CH2:7][Cl:1])[CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 765833-BromobenzaldehydeHCID 73680070[(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride

Product 1

HCID 540158261-(3-Bromophenyl)-7-chloro-1-hepten-3-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2 parts of [(tetrahydro-2H-pyran-2-ylidene)methyl] triphenylphosphonium chloride and 1.85 parts of 3-bromobenzaldehyde were combined in 45 parts of xylene. This was maintained under a nitrogen atmosphere and was refluxed for 3 hours. After the reaction mixture was cooled to room temperature, xylene was removed at a temperature of about 60° C. and under reduced pressure, leaving a product mixture. This mixture was separated chromatographically on a silica column using benzene as the elution solvent, to yield 1-(3-bromophenyl)-7-chloro-1-hepten-3-one.

Workup

  1. temperatureThis was maintained under a nitrogen atmosphere
  2. temperaturewas refluxed for 3 hours
  3. customxylene was removed at a temperature of about 60° C. and under reduced pressure
  4. customleaving a product mixture
  5. customThis mixture was separated chromatographically on a silica column

Sources & evidence

ORD record
ord-35f440df14024a91bd8fc301d5da4a63
Source dataset
uspto-grants-1982_08
Patent number
US04347192

Reaction notes

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