Methanol → Methyl 3-carbomethoxy-4-fluorobenzaldehyde

HRID 2975

Reaction equation

HRID 2975 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].CN([CH:14]=[O:15])C.C(N([CH2:21][CH3:22])CC)C.C[OH:24]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:7]1[C:22]([C:21]([O:15][CH3:14])=[O:24])=[C:9]([F:10])[CH:2]=[CH:3][C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 19688468Methyl 3-carbomethoxy-4-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

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.

Workup

  1. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-d9642a5bf49d4ae5ab36a31093ec85a4
Source dataset
uspto-grants-1998_03
Patent number
US05731432

Linked notes

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