5-Bromo-2-methylbenzaldehyde → 4-Bromo-2-(4-methoxy-but-1-enyl)-1-methyl-benzene

HRID 1809820Notes

Reaction equation

HRID 1809820 reaction equation
[Br-].[CH3:2][O:3][CH2:4][CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:35])=[C:31]([CH:34]=1)[CH:32]=O.CC#N.O>CC#N>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:35])=[C:31]([CH:32]=[CH:6][CH2:5][CH2:4][O:3][CH3:2])[CH:34]=1

Participants

5

Reactant 3

HCID 104202895-Bromo-2-methylbenzaldehydeHCID 18373917Acetonitrile--water (1/1)HCID 21458797(3-Methoxypropyl)triphenylphosphonium bromide

Product 1

HCID 675427464-Bromo-2-(4-methoxy-but-1-enyl)-1-methyl-benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound is prepared analogously as described for the title B compound in Example 45 using (3-methoxy-propyl)-triphenyl-phosphonium bromide and 5-bromo-2-methyl-benzaldehyde (prepared in Example 48; containing 20% of 3-bromo-2-methyl-benzaldehyde): Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 6.60 min.

Workup

  1. custom6.60 min.

Sources & evidence

ORD record
ord-e95f9b3acf00491c96d0f61f6b94fe4e
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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