Boron tribromide → HCID 131721741, compound

HRID 1637792Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:19]3[CH:24]=[CH:23][C:22]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)[C@H:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:19]3[CH:24]=[CH:23][C:22]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)[C@H:8]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In dry glassware and under a nitrogen atmosphere, (+,-) cis Methanesulfonic acid 4-(7-methoxy-3-phenyl-chroman-4-yl)-phenyl ester (5.0 g, 12.2 mmol) was dissolved in dry methylene chloride (150 ml), and cooled to -78° C. A solution of 1M boron tribromide in methylene chloride was added dropwise with stirring at such a rate that the temperature did not exceed -70° C. The reaction mixture was stirred at -78° C. for 60 min, and for 60 min. after the cooling was removed. A 5% sodium bicarbonate solution (100 ml) was slowly added, and the mixture extracted with ethyl acetate (300+2×25 ml). The combined organic extracts were washed with water and brine, dried (magnesium sulphate) and evaporated.

Workup

customdid not exceed -70° C
stirringThe reaction mixture was stirred at -78° C. for 60 min
customfor 60 min. after the cooling was removed
additionA 5% sodium bicarbonate solution (100 ml) was slowly added
extractionthe mixture extracted with ethyl acetate (300+2×25 ml)
washThe combined organic extracts were washed with water and brine
dry with materialdried (magnesium sulphate)
customevaporated

Sources & evidence

ORD record: ord-dd003b958aa1444c9f776c179d8bc34d
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043269

Reaction notes

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