Triphenylphosphine → 4-Bromo-2-(trifluoromethyl)-1H-indole

HRID 888907Notes

Reaction equation

HRID 888907 reaction equation
[Br:1][C:2]1[C:3]([CH2:15]Br)=[C:4]([NH:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:15]=[C:9]([C:10]([F:13])([F:12])[F:11])[NH:8]2

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 59151288HCID 59151288, compound

Product 1

HCID 534025934-Bromo-2-(trifluoromethyl)-1H-indoleYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-(3-bromo-2-bromomethyl-phenyl)-2,2,2-trifluoro-acetamide (2.9 g) in toluene (40 mL) was treated with triphenylphosphine (2.3 g, 8.7 mmol). The solution was stirred at 60° C. for 2 h, then cooled to 0° C. The beige solid that precipitated was collected by filtration, washed with diethyl ether, then dissolved in DMF (60 mL), and heated to reflux under nitrogen for 16 h. The reaction mixture was evaporated to dryness, then partitioned between EtOAc and a sat. sodium carbonate solution. The organic layer was isolated, dried (MgSO4), and purified by column chromatography to give the title compound as a yellow solid (1.55 g, 84%).

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe beige solid that precipitated was collected by filtration
  3. washwashed with diethyl ether
  4. dissolutiondissolved in DMF (60 mL)
  5. temperatureheated
  6. temperatureto reflux under nitrogen for 16 h
  7. customThe reaction mixture was evaporated to dryness
  8. custompartitioned between EtOAc
  9. customThe organic layer was isolated
  10. dry with materialdried (MgSO4)
  11. custompurified by column chromatography

Sources & evidence

ORD record
ord-bdfd452bd3c14405bf9bfd8662987259
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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