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

HRID 857021Notes

Reaction equation

HRID 857021 reaction equation
[Li][CH2:2]CCC.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[F:15])[CH:10]=O>C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH2:2])[CH:12]=[CH:13][C:14]=1[F:15]

Participants

4

Reactant 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 218646502-Bromo-4-ethenyl-1-fluorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of Ph3PCH3Br (57 g) in THF (240 mL) at 0° C. was dropwise added n-BuLi (1.6 N, 100 mL). The resulting mixture was allowed to warm to room temperature and stirred for 1 h. After recooling to 0° C., a solution of 3-bromo-4-fluoro-benzaldehyde (20.3 g) in THF (20 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched with water, concentrated, and extracted with methylene chloride. The combined organic layers were dried over magnesium sulfate, concentrated under vacuum. The crude product was purified by flash chromatography eluting with 10% ethyl acetate in hexanes to give the title compound as an oil (18 g).

Workup

  1. customAfter recooling to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 h
  4. customThe reaction mixture was quenched with water
  5. concentrationconcentrated
  6. extractionextracted with methylene chloride
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude product was purified by flash chromatography
  10. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-67f81e632b2240c59db54c3956699f73
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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