Water → HCID 21998708, compound

HRID 1976792Notes

Reaction equation

HRID 1976792 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]([F:22])([F:21])[F:20])[CH:13]=[CH:12]2)C1C=CC=CC=1.B(Br)(Br)Br.O>ClCCl>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]([F:22])([F:20])[F:21])[CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 21998712HCID 21998712, compound

Product 1

HCID 21998708HCID 21998708, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-benzyloxy-1-(2,2,2-trifluoroethyl)indole (1.56 g, 4.09 mmol) in dichloromethane (10 mL) at 0° C. was treated dropwise with 1M BBr3 in dichloromethane(5.73 mL, 5.73 mmol), stirred for 2 hours, transferred to 2:1:1 water/10% NaHCO3/brine (100 mL), and extracted with ethyl acetate (100 mL). The extract was washed with brine (40 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography with 9:1 hexane/ethyl acetate to provide 118 mg of the desired product.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe extract was washed with brine (40 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography with 9:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-2be63a7246964ac5802efb9d102a1456
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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