Water → HCID 59066525, compound

HRID 1837956Notes

Reaction equation

HRID 1837956 reaction equation
[Cl-].[F:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[Li]CCCC.[Br:34][C:35]1[S:39][C:38]([CH:40]=O)=[CH:37][CH:36]=1.O>C1COCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:7]=[CH:40]\[C:38]2[S:39][C:35]([Br:34])=[CH:36][CH:37]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 784285-Bromothiophene-2-carbaldehydeHCID 2733554(4-Fluorobenzyl)triphenylphosphonium chlorideHCID 178418339Butyllithium

Product 1

HCID 59066525HCID 59066525, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. suspension of 4-fluorobenzyl triphenylphosphonium chloride (1.82 g, 4.47 mmol) in THF (20 mL) was added a solution of n-BuLi (2.5M in hexane, 1.8 mL, 4.47 mmol) and the reaction mixture was stirred for 1 h. 5-Bromothiophene-2-carbaldehyde was added, the reaction was allowed to warm to room temperature and stirred for 1 h. The resulting mixture was treated with water and extracted with Et2O. The crude product was purified by preparative TLC (30% EtOAc/hex) to give 5-[(1Z)-2-(4-fluorophenyl)vinyl]-2-bromothiophene (170 mg, 13%) as a colorless oil: 1H NMR (CDCl3) δ 6.51 (d, J=11.9 Hz, 1H), 6.59 (d, J=11.9 Hz, 1H), 6.72 (d, J=4.3 Hz, 1H), 6.85 (d, J=3.8 Hz, 1H), 7.04-7.11 (m, 2H), 7.27-7.33 (m, 2H) and 5-[(1E)-2-(4-fluorophenyl)vinyl]-2-bromothiophene (200 mg, 16%) as a white solid: 1H NMR (CDCl3) δ 6.74-6.80 (m, 2H), 6.95-7.07 (m, 4H), 7.39-7.44 (m, 2H).

Workup

  1. stirringstirred for 1 h
  2. extractionextracted with Et2O
  3. customThe crude product was purified by preparative TLC (30% EtOAc/hex)

Sources & evidence

ORD record
ord-494d287911ab49ea83dd642c5c128e4a
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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