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

HRID 45521Notes

Reaction equation

HRID 45521 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-fe56ed9758f84238bce4fa450bf5dc4e
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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