Methanol → HCID 86738867, compound

HRID 851285Notes

Reaction equation

HRID 851285 reaction equation
CO.C[O:4][CH:5]([O:8]C)OC.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=[O:15]>C1(C)C=CC=CC=1>[CH3:18][CH:11]([CH3:12])[C:5]([OH:8])=[O:4].[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 86738867HCID 86738867, compoundYield 162.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

1.5 g of air-dried ion exchanger SPC 118 (H-form of a cation exchanger, strongly acid, macroporous), 16 g (0.5 mole) of methanol and 58.5 g (0.55 mole) of orthoformic acid trimethyl ester were added to a solution of 101.5 g (0.5 mole) of 3-bromo-4-fluorobenzaldehyde in 200 ml of toluene, the mixture was stirred for a further 1 hour without a bath and was then warmed at 50° C. for 2 hours. The reaction mixture was cooled, filtered to remove the ion exchanger and washed with 200 ml of 5% strength potassium carbonate solution. The solvent was then stripped off and the residue was distilled in vacuo. 118 g (95% of theory) of 3-bromo-4-fluorobenzaldehyde dimethyl acetate were obtained in this way, in the form of a colorless liquid with a boiling point of 68° C./0.1 mm Hg.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customto remove the ion exchanger
  4. washwashed with 200 ml of 5% strength potassium carbonate solution
  5. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-f1e415a7d69e4eae8db214d9a117ec2b
Source dataset
uspto-grants-1983_05
Patent number
US04383949

Reaction notes

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