Toluene → HCID 58155200, compound

HRID 1929468Notes

Reaction equation

HRID 1929468 reaction equation
[K].[Br:2][C:3]1[CH:4]=[CH:5][C:6]([F:14])=[C:7]([C:9]([CH:11]2[CH2:13][CH2:12]2)=O)[CH:8]=1.[C:15]1(C)C=CC=CC=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([F:14])=[C:7]([C:9]([CH:11]2[CH2:13][CH2:12]2)=[CH2:15])[CH:8]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 5462222PotassiumHCID 53405397(5-Bromo-2-fluorophenyl)(cyclopropyl)methanone

Product 1

HCID 58155200HCID 58155200, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Conditions

Temperature
0 °C

Procedure

A suspension of methyltriphenylphosphonium bromide (7.142 g, 20 mmol) in toluene (50 ml) was treated with potassium amylate (1.7 M in toluene, 11.76 ml, 20 mmol), and the mixture was stirred at 0° C. for 30 minutes. A solution of (5-bromo-2-fluoro-phenyl)-cyclopropyl-methanone (4.05 g, 17 mmol) in toluene (17 ml) was added and the mixture stirred at room temperature for 2 hours. For the workup, the mixture was extracted with water and ethyl acetate, the organic layer separated, dried and evaporated at reduced pressure. After chromatography on silica gel using a mixture of hexane and ethyl acetate as the eluent, the 4-bromo-2-(1-cyclopropyl-vinyl)-1-fluoro-benzene was obtained as yellow oil (3.816 g, 95% of theory). Mass (calculated) C11H10BrF [241.102]; (found) [M+H]+=241, [M+2-H]+=243.

Workup

  1. stirringthe mixture stirred at room temperature for 2 hours
  2. extractionFor the workup, the mixture was extracted with water and ethyl acetate
  3. customthe organic layer separated
  4. customdried
  5. customevaporated at reduced pressure
  6. additionAfter chromatography on silica gel using a mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-c3d9d6ae94094a0cb9335a07eb904ef5
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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