Boron tribromide → 2-Trifluoromethyl-n-[4-(6-hydroxy-1,3-benzothiazol-2-yl)phenyl]-4-(hydroxy)benzamide

HRID 339540Notes

Reaction equation

HRID 339540 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:28]=[C:27]([O:29]C)[CH:26]=[CH:25][C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23]C)[CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][CH:9]=1)=[O:6].B(Br)(Br)Br.C(Cl)Cl.CO>C(Cl)Cl>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:4]=1[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:12][CH:13]=1)=[O:6]

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 21226129Dichloromethane methanolHCID 672404602-Trifluoromethyl-n-[4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-4-(methoxy)benzamide

Product 1

HCID 672409112-Trifluoromethyl-n-[4-(6-hydroxy-1,3-benzothiazol-2-yl)phenyl]-4-(hydroxy)benzamideYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared as described in the Demethylation section using 2-trifluoromethyl-N-[4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-4-(methoxy)benzamide (0.30 g, 0.655 mmol) in dry DCM (15 ml) and BBr3 (1.0M in DCM, 1.4 ml, 1.4 mmol) at −78° C. under an atmosphere of argon. Stirring was continued at −78° C. for 1 h, and then the reaction mixture was allowed to rise to room temperature overnight. A further volume of BBr3 (1.0 M in DCM, 1.4 ml, 1.4 mmol) was added and the reaction mixture stirred at room temperature for 24 h to give the title compound (0.175 g, 62%) as a colourless solid after work-up and flash chromatography (15:1 DCM/MeOH).

Workup

  1. customPrepared
  2. customat −78° C.
  3. waitto rise to room temperature overnight
  4. stirringthe reaction mixture stirred at room temperature for 24 h

Sources & evidence

ORD record
ord-dcd4a029e6f54de8890999571f608333
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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