Boron tribromide → HCID 21848298, compound

HRID 618715Notes

Reaction equation

HRID 618715 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12]C)[C:7]=1[CH2:14][CH2:15][CH3:16]>ClCCl>[F:5][C:6]1[C:7]([CH2:14][CH2:15][CH3:16])=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21848323HCID 21848323, compound

Product 1

HCID 21848298HCID 21848298, compoundYield 559.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

24 ml (24 mmol) of a 1M boron tribromide solution in dichloromethane were added at -78° to a solution of 3.36 mmol (20 mmol) of 1-fluoro-3-methoxy-2-propyl-benzene in 25 ml of dichloromethane and the mixture was stirred for 10 minutes. After warming to room temperature the mixture was poured cautiously on to 100 ml of ice-water and extracted twice with 250 ml of dichloromethane each time. After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane/hexane 4:1). There were obtained 2.9 g (94%) of 3-fluoro-2-propyl-phenol as a pale yellow oil.

Workup

  1. extractionextracted twice with 250 ml of dichloromethane each time
  2. dry with materialAfter drying over sodium sulfate concentration
  3. customThe crude product obtained
  4. customwas purified by column chromatography on silica gel (dichloromethane/hexane 4:1)

Sources & evidence

ORD record
ord-4eff0cb9d8cd4f00bf570d3ee8d46b06
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

Loading…