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

HRID 891963Notes

Reaction equation

HRID 891963 reaction equation
[Li][CH2:2]CCC.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:14]=1)[CH:12]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCCCCC.C(OCC)(=O)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:12]=[CH2:2])[CH:14]=1

Participants

6

Reactant 2

HCID 7363275-Bromo-2-fluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 219339834-Bromo-2-ethenyl-1-fluorobenzeneYield 72%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a suspension of methyl(triphenyl)-phosphonium bromide (15.5 g, 43 mmol) in THF (60 ml) were added at −78° C. BuLi (27 ml, 1.6 M in hexane, 43.2 mmol) and 5-bromo-2-fluoro-benzaldehyde (877 mg, 43 mmol). The reaction mixture was stirred 18 hours at r.t. After work-up and purification by chromatography (hexane/ethyl acetate 9/1 to 4/1) 5.7 g (28.5 mmol, 72%) of the title compound were obtained, 1H-NMR (300 MHz, CDCl3): δ=7.62 (dd, 1H), 7.26-7.36 (m, 1H), 6.93 (t, 1H), 6.79 (dd, 1H), 5.42 (d, 1H).

Workup

  1. additionwere added at −78° C

Sources & evidence

ORD record
ord-8b265f876d1744fda9b030b9a4e2881f
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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