Boron tribromide → HCID 12299666, compound

HRID 1609224Notes

Reaction equation

HRID 1609224 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 345014Cyclohexyl(4-methoxyphenyl)methanone

Product 1

HCID 12299666HCID 12299666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11 g (50.4 mmol) of 4-methoxyphenyl cyclohexyl ketone in 730 ml of dichloromethane p.a. is treated at -70° C. under argon with 101 ml of a 1M solution of boron tribromide (101 mmol) in dichloromethane and then left at room temperature for 18 h. It is concentrated in vacuo, the residue is taken up with 500 ml of ethanol and 80 ml of water and the mixture is heated under reflux for 3 h. After concentration in vacuo, the residue is taken up in dichloromethane, and the organic phase is washed with water, dried over sodium sulphate and concentrated to dryness in vacuo. The crude product is chromatographed on silica gel using dichloromethane/methanol (20:1).

Workup

  1. concentrationIt is concentrated in vacuo
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 3 h
  4. concentrationAfter concentration in vacuo
  5. washthe organic phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness in vacuo
  8. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-11fc8fabac6c4be0822c6c04711894f7
Source dataset
uspto-grants-1995_03
Patent number
US05399698

Reaction notes

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