Boron tribromide → HCID 58319168, compound

HRID 2363150Notes

Reaction equation

HRID 2363150 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH:6]=[C:7]2[C:12]([F:15])([F:14])[F:13].B(Br)(Br)Br>C(Cl)Cl>[F:13][C:12]([F:14])([F:15])[C:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:3]([OH:2])[C:4]=2[CH2:5][CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58319207HCID 58319207, compound

Product 1

HCID 58319168HCID 58319168, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-methoxy-1-trifluoromethyl-indan-1-ol (170 mg, 0.73 mmol) in benzene (4 mL) was added p-toluenesulfonic acid (139 mg, 0.73 mmol). The mixture was stirred overnight at 80° C., and concentrated under reduced pressure. The crude residue was purified by column chromatography to give 4-methoxy-1-trifluoromethyl-3H-inden. The 4-methoxy-1-trifluoromethyl-3H-inden was dissolved in CH2Cl2 (2 ml) and 1M-BBr3 (in CH2Cl2, 1.46 mL, 1.46 mmol) was added dropwise. The mixture was stirred for 1 hour at room temperature, and then washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography to give 1-trifluoromethyl-3H-inden-4-ol (70 g, 48%).

Workup

  1. washwashed with saturated ammonium chloride, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-2c986c69325e4e199ee423413f23a390
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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