5-Bromo-2-methylbenzaldehyde → 4-Bromo-2-(3-methoxy-propenyl)-1-methyl-benzene

HRID 2354976Notes

Reaction equation

HRID 2354976 reaction equation
[Br-].[CH3:2][O:3][CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:34])=[C:30]([CH:33]=1)[CH:31]=O.CCCCCC.CCOC(C)=O.CC#N.O>CC#N>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:34])=[C:30]([CH:31]=[CH:5][CH2:4][O:3][CH3:2])[CH:33]=1

Participants

6

Reactant 4

HCID 104202895-Bromo-2-methylbenzaldehydeHCID 18373917Acetonitrile--water (1/1)HCID 21226206Ethyl acetate hexaneHCID 22377376(2-Methoxy-ethyl)-triphenyl-phosphonium, bromide

Product 1

HCID 675436394-Bromo-2-(3-methoxy-propenyl)-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 (2-methoxy-ethyl)-triphenyl-phosphonium bromide (prepared in Example 46) and the title A compound, 5-bromo-2-methyl-benzaldehyde (containing 20% of 3-bromo-2-methyl-benzaldehyde) (6 g, 30.14 mmol): TLC, Rf (hexane/AcOEt 9/1)=0.48. Rt (HPLC, Nucleosil C 8, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 6.26, 6.34 min.

Workup

  1. custom6.26, 6.34 min.

Sources & evidence

ORD record
ord-f03ffed4379d41f2b76557375c692974
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

Loading…