Phosphorus tribromide → 6-Methoxy-3-(trifluoromethyl)indene

HRID 1634346Notes

Reaction equation

HRID 1634346 reaction equation
O[C:2]1([C:13]([F:16])([F:15])[F:14])[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.P(Br)(Br)Br>O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([C:13]([F:14])([F:15])[F:16])=[CH:3][CH2:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 186776465-methoxy-1-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 186776456-Methoxy-3-(trifluoromethyl)indeneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred Compound 62(850 mg, 3.66 mmol) was added PBr3(9.90 g, 36.6 mmol) with ice-cooling. The reaction mixture was stirred at 80° C. for 6 h. The mixture was diluted with water with ice-cooling and extracted with CH2Cl2. The combined solution was washed with sat. NaHCO3 and brine, dried(MgSO4) and concentrated in vacuo to give crude product as a yellow oil. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(50:1-40:1) to give Compound 63(727 mg, 93%) as a yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with CH2Cl2
  4. washThe combined solution was washed with sat. NaHCO3 and brine, dried(MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give crude product as a yellow oil
  7. customThe crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(50:1-40:1)

Sources & evidence

ORD record
ord-e3a3d97ee2464d67828d8f20af2a0a98
Source dataset
uspto-grants-2003_01
Patent number
US06506775B1

Reaction notes

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