Benzaldehyde, 3-(4-fluorophenoxy)- → HCID 19779540, compound

HRID 2082087Notes

Reaction equation

HRID 2082087 reaction equation
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=O)=[CH:10][CH:9]=1>CCOCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[CH2:1])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 3085320Benzaldehyde, 3-(4-fluorophenoxy)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 19779540HCID 19779540, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of potassium tert-butoxide (2.61 g, 23.3 mmol) in ether (100 mL) was added methyltriphenylphosphonium bromide (8.34 g, 23.3 mmol) and the solution was brought to reflux for 15 min. It was then cooled to 0° C. and 3-(4-fluorophenoxy)benzaldehyde (4.80 g, 22.2 mmol) was added. The reaction was stirred for 5 min at 0° C., the cooling bath was withdrawn and the reaction allowed to warm to ambient temperature and stir for 45 min. It was then filtered through Celite and concentrated. The resulting residue was chromatographed (silica gel; hexanes, ether 96:4) to afford 4.09 g (86%) of 3-(4-fluorophenoxy)styrene as a colorless oil.

Workup

  1. temperatureto reflux for 15 min
  2. customthe cooling bath was withdrawn
  3. temperatureto warm to ambient temperature
  4. stirringstir for 45 min
  5. filtrationIt was then filtered through Celite
  6. concentrationconcentrated
  7. customThe resulting residue was chromatographed (silica gel; hexanes, ether 96:4)

Sources & evidence

ORD record
ord-4ab62eef6a3244c8a774013b3b74d34c
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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