Boron tribromide → 5-chloro-2-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-phenol

HRID 1875744Notes

Reaction equation

HRID 1875744 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:11]3[CH:20]=[C:21]([F:25])[C:22]([F:24])=[CH:23][C:10]=3[N:9]=2)=[C:4]([O:26]C)[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[C:11]3[CH:20]=[C:21]([F:25])[C:22]([F:24])=[CH:23][C:10]=3[N:9]=2)=[C:4]([OH:26])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67049962HCID 67049962, compound

Product 1

HCID 1363784785-chloro-2-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-phenolYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-chloro-2-methoxy-phenyl)-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole (1.95 g, 5 mmol) in dichloromethane (40 ml) was added boron tri bromide (1M solution in dichloromethane; 21 ml, 21 mmol) at 25° C., and the resulting mixture was allowed to stir for 16 h at the same temperature. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate solution and further diluted with dichloromethane (30 ml). The organic layer was washed with water, and then with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to afford the crude material. Crude product was purified by column chromatography using silica gel (5-10% ethyl acetate/n-hexane) to give the desired compound as a colorless powder (62%). MS (Turbo Spray): m/z=376.9 (M+H).

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate solution
  2. additionfurther diluted with dichloromethane (30 ml)
  3. washThe organic layer was washed with water
  4. dry with materialwith brine, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto afford the crude material
  8. customCrude product was purified by column chromatography

Sources & evidence

ORD record
ord-a5f07c8a2f8d41e9867e5065c61d2e00
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

Loading…