Boron tribromide → 3-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol

HRID 1771589Notes

Reaction equation

HRID 1771589 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 89443597N-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline

Product 1

HCID 894450523-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenolYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[[2-fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline (512 mg, 1.60 mmol, 1.0 eq) in CH2Cl2 (10 mL) at −70° C. was added BBr3 (0.6 mL, 65.3 mmol, 40.8 eq). The reaction was warmed to room temperature and stirred for 1 h. The reaction was then cooled to 0° C. and quenched by addition of water. The pH of the solution was adjusted to pH 7 with aqueous Na2CO3, then extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a colourless oil (460 mg, 94%).

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. customquenched by addition of water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c197a857634c4639afd8b1b32b465956
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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