Water → 1-[2-(4-Fluorophenyl)ethenyl]-3,5-dimethoxybenzene

HRID 1968406Notes

Reaction equation

HRID 1968406 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1.[OH-].[Na+].O>C(Cl)Cl>[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH:7][C:6]2[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=[C:4]([O:3][CH3:2])[CH:5]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 10962038(3,5-Dimethoxybenzyl)triphenylphosphonium bromide

Product 1

HCID 699010781-[2-(4-Fluorophenyl)ethenyl]-3,5-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3,5-dimethoxybenzyl)triphenylphosphonium bromide (300 mg, 0.6 mM), 4-fluorobenzaldehyde (133 mg, 1.07 mM), catalytic amounts of 18 crown-6 in DCM was added 1.5 mL of 50% solution of NaOH. The reaction was stirred for 5 h and water was added. The water phase was extracted with ethyl acetate and the organic phase was combined. The crude product was purified through flash chromatography eluting with hexanes/ethyl acetate (98:2).

Workup

  1. extractionThe water phase was extracted with ethyl acetate
  2. customThe crude product was purified through flash chromatography
  3. washeluting with hexanes/ethyl acetate (98:2)

Sources & evidence

ORD record
ord-20a1444f9c434604ac7a57f065d89a43
Source dataset
uspto-grants-2013_04
Patent number
US08426369B2

Reaction notes

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