Boron tribromide → Ethyl 3-(1-(4-bromobenzyl)-6-hydroxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

HRID 1848733Notes

Reaction equation

[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([O:16]C)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][CH:3]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:18][C:19]([CH3:25])([CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of ethyl 3-(1-(4-bromobenzyl)-6-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (12 g, 27 mmol) in DCM (200 mL) was added BBr3 (20 g, 81 mmol) in DCM (100 mL) drop wise at −78° Celsius. The solution was gradually warmed to 5° Celsius and stirred for 3 h. The reaction mixture was slowly added to saturated NaHCO3 with rapid stirring for 1 h. The organic phase was separated and aqueous phase was extracted with DCM (200 mL). The combined organic phases were dried over Na2SO4, filtered, concentrated to dryness and purified by FCC to provide the title compound. MS (ESI): mass calcd. for C21H23BrN2O3, 430.09; m/z found, 438 [M+H]+.

Workup

stirringwith rapid stirring for 1 h
customThe organic phase was separated
extractionaqueous phase was extracted with DCM (200 mL)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness
custompurified by FCC

Sources & evidence

ORD record: ord-b355d2a73272492fb1433438377e49d9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952177B2

Reaction notes

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