Boron tribromide → 4-[1-(4-Bromophenyl)-2-(methylamino)ethyl]phenol

HRID 2361795Notes

Reaction equation

HRID 2361795 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[CH2:13][NH:14][CH3:15])=[CH:8][CH:7]=1>ClCCl.C([O-])(O)=O.[Na+]>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[CH2:13][NH:14][CH3:15])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 59331929HCID 59331929, compound

Product 1

HCID 593319284-[1-(4-Bromophenyl)-2-(methylamino)ethyl]phenol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Boron tribromide (7.8 ml, 1.0M in dichloromethane) was added slowly to a solution of [2-(4-Bromo-phenyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-amine (500 mg, 1.56 mmol) in dichloromethane (8 ml) at 0° C., under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and then stirred for a further hour. The mixture was poured on to ice and then diluted with dichloromethane and saturated NaHCO3 solution. The organic layer was dried (MgSO4), filtered and concentrated to afford the desired product. LC/MS: (PS-B3) Rt 2.76 [M+H]+ 306.

Workup

  1. additionThe mixture was poured on to ice
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-85086cde824b4c89b06baeeb0b920f40
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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