4-Bromo-2-fluorobenzaldehyde → 4-Bromo-1-ethenyl-2-fluorobenzene

HRID 2415251Notes

Reaction equation

HRID 2415251 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[CH3:11]C(C)([O-])C.[K+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:11])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 2

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 166607744-Bromo-1-ethenyl-2-fluorobenzene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of 4-bromo-2-fluoro-benzaldehyde (Aldrich, 2.30 g, 11.3 mmol) and methyltriphenylphosphonium bromide(Aldrich, 4.93 g, 13.6 mmol) in ether (50 mL), potassium tert-butoxide(1.52 g, 13.6 mmol) was added and the mixture was stirred at room temperature for 1 hour. The solid was filtered off and the filtrate was concentrated. The residue was treated with 30% ethyl acetate/hexanes (3 mL) and the solid was removed by filtration. The filtrate was filtered through a silica gel pad eluting with 30% ethyl acetate/hexanes to give a yellow oil. 1.54 g, 68%.

Workup

  1. additionwas added
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was treated with 30% ethyl acetate/hexanes (3 mL)
  5. customthe solid was removed by filtration
  6. filtrationThe filtrate was filtered through a silica gel pad
  7. washeluting with 30% ethyl acetate/hexanes
  8. customto give a yellow oil

Sources & evidence

ORD record
ord-9bb0f0add52e4ea8827cf3376e87c87a
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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