1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Bromo-1-ethenyl-2-fluorobenzene

HRID 661214Notes

Reaction equation

HRID 661214 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.N12CCCN=C1CCCC[CH2:12]2>ClCCl.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:12])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

10.0 g (49.3 mmol) of 4-bromo-2-fluorobenzaldehyde were dissolved in 40 ml of dichloromethane, admixed with 9.6 ml (9.7 g, 64.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 19.4 g (54.2 mmol) of methyltriphenylphosphonium bromide and stirred at RT for 3 h. The reaction mixture was purified on silica gel (eluent: dichloromethane). The product fractions were combined, concentrated under reduced pressure and dried under high vacuum. Yield: 4.5 g (41% of theory)

Workup

  1. customThe reaction mixture was purified on silica gel (eluent: dichloromethane)
  2. concentrationconcentrated under reduced pressure
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-faae670b9ace4328af610963ccf189b7
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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