Reaction #3071

ord-d9642a5bf49d4ae5ab36a31093ec85a4

Reaction equation

O=Cc1ccc(F)c(Br)c1
3-bromo-4-fluorobenzaldehyde
CN(C)C=O
DMF
CCN(CC)CC
triethylamine
CO
MeOH
→
COC(=O)c1c(F)ccc(C=O)c1C
methyl 3-carbomethoxy-4-fluorobenzaldehyde

Reactants

O=Cc1ccc(F)c(Br)c1
3-bromo-4-fluorobenzaldehyde
CN(C)C=O
DMF
CCN(CC)CC
triethylamine
CO
MeOH

Reagents

c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Pd(PPh3)4

Conditions

Temperature
90°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ExtractionExtraction and chromatography

Procedure

A mixture of 1.0 mmol of 3-bromo-4-fluorobenzaldehyde, 4 mL of DMF, 0.2 mL of triethylamine, 0.4 mL of MeOH and 0.05 mmol of Pd(PPh3)4 was heated at 90° C. at 40 psi under CO atmosphere for 16 h. Extraction and chromatography provided methyl 3-carbomethoxy-4-fluorobenzaldehyde.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731432uspto-grants-1998_03