Boron tribromide → HCID 57708912, compound

HRID 547136Notes

Reaction equation

B(Br)(Br)Br.[CH3:5][O:6][C:7](=[O:43])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH2:39][CH3:40])([C:24]3[CH:29]=[CH:28][C:27]([O:30][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])=[C:26]([CH3:38])[CH:25]=3)[CH2:22][CH3:23])=[CH:17][C:16]=2[O:41]C)=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:5][O:6][C:7](=[O:43])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH2:22][CH3:23])([C:24]3[CH:29]=[CH:28][C:27]([O:30][S:31]([C:34]([F:37])([F:35])[F:36])(=[O:32])=[O:33])=[C:26]([CH3:38])[CH:25]=3)[CH2:39][CH3:40])=[CH:17][C:16]=2[OH:41])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A 1 M solution of boron tribromide in dichloromethane (0.15 mL, 0.15 mmol) was added to a solution of {4′-[1-ethyl-1-(3-methyl-4-trifluoromethanesulfonyloxy-phenyl)-propyl]-2′-methoxy-biphenyl-4-yl}-acetic acid methyl ester (Example 176-(7); 20 mg, 0.0366 mmol) in dichloromethane (0.2 mL) at −78° C., and the mixture was stirred at −78° C. for 30 minutes. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane:ethyl acetate=3:1) to give the title compound (10.8 mg, 55%).

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (hexane only to hexane

Sources & evidence

ORD record: ord-7aaa4ddc9e5044738477acad02897446
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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