3-Iodo-4-methylbenzaldehyde → 3-Iodo-4-methylstyrene

HRID 2974

Reaction equation

HRID 2974 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=O.[Li][CH2:12]CCC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=[CH2:12]

Participants

5

Reactant 2

HCID 123302543-Iodo-4-methylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 196884243-Iodo-4-methylstyrene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

This aldehyde (1 mmol)was added to a premixed solution of 1.5 mmol of methyl triphenylphosphonium bromide and 1.2 mmol of n-BuLi in 5 mL of THF at 0° C. and this mixture was stirred for 3-6 h at rt and then processed by extraction and chromatography to give 3-iodo-4-methylstyrene.

Workup

  1. extractionprocessed by extraction and chromatography

Sources & evidence

ORD record
ord-e65eb05600a341c1a97cfb8e1984da81
Source dataset
uspto-grants-1998_03
Patent number
US05731432

Linked notes

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