4-Bromo-2-fluorobenzaldehyde → 2-(4-Bromo-2-fluorophenyl)vinyl methyl ether

HRID 385703Notes

Reaction equation

HRID 385703 reaction equation
[Cl-].[C:2]1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[C:22]([O-:25])(C)C.[K+].[Br:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[C:30]([F:36])[CH:29]=1>O1CCCC1>[CH3:2][O:25][CH:22]=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([Br:27])=[CH:29][C:30]=1[F:36]

Participants

5

Reactant 3

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 9882740Triphenylphosphine hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 670278822-(4-Bromo-2-fluorophenyl)vinyl methyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methoxymethyl)triphenylphosphonium chloride (147 g, 0.48 mol) was suspended in tetrahydrofuran (1.5 L) under an argon atmosphere, and cooled to 0° C. t-BuOK (51.6 g, 0.46 mol) was added in portions. A solution of 4-bromo-2-fluorobenzaldehyde (40.6 g, 0.2 mol) in tetrahydrofuran (500 mL) was then added to the reaction mixture. The solution was stirred at room temperature for 1 hour. The solution was poured into ice-water and extracted with ethyl acetate (2×). The combined organic phases were dried and concentrated in vacuo. Purification via flash chromatography afforded the title compound.

Workup

  1. additionwas added in portions
  2. extractionextracted with ethyl acetate (2×)
  3. customThe combined organic phases were dried
  4. concentrationconcentrated in vacuo
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-d8f01313bb9c4786bb774f8116a612d5
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…