Methoxymethyl-triphenylphosphonium chloride → 2-(4-Bromo-2,6-difluorophenyl)vinyl methyl ether

HRID 1799533Notes

Reaction equation

HRID 1799533 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[Br:30][C:31]1[CH:38]=[C:37]([F:39])[C:34]([CH:35]=O)=[C:33]([F:40])[CH:32]=1>O1CCCC1>[CH3:2][O:3][CH:4]=[CH:35][C:34]1[C:37]([F:39])=[CH:38][C:31]([Br:30])=[CH:32][C:33]=1[F:40]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 27732904-Bromo-2,6-difluorobenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 670276252-(4-Bromo-2,6-difluorophenyl)vinyl methyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(Methoxymethyl)triphenylphosphonium chloride (1133 g, 3.7 mol) was suspended in tetrahydrofuran (7.0 L) under argon atmosphere, and stirred with ice-water cooling. t-BuOK (397 g, 3.54 mol) was added in portions. Then a solution of 4-bromo-2,6-difluorobenzaldehyde (340 g, 1.54 mol) in tetrahydrofuran (2.7 L) was added and the reaction was stirred at room temperature for 6 hours. The solution was then poured into ice-water and extracted with ethyl acetate (2×). The combined organic phases were dried and concentrated in vacuo. This material was purified by flash chromatography to afford the title compound.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. customThe combined organic phases were dried
  3. concentrationconcentrated in vacuo
  4. customThis material was purified by flash chromatography

Sources & evidence

ORD record
ord-53107992e3b04bd38642de4edc9f19bc
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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