Boron tribromide → HCID 178474486, compound

HRID 1722011Notes

Reaction equation

B(Br)(Br)Br.[C:5]([NH:8][C:9]1[NH:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[N:11][C:10]=1[CH3:22])(=[O:7])[CH3:6]>C(Cl)Cl>[C:5]([NH:8][C:9]1[NH:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:11][C:10]=1[CH3:22])(=[O:7])[CH3:6]

Participants

Conditions

Temperature: -78 °C

Procedure

Methylene chloride, 125 ml was stirred and cooled to -78° C. in an acetone-dry ice bath. Boron tribromide (7.5 ml, 0.079 mole) was added, followed by 42 (6.15 g, 0.025 mole). After a 10 minutes period at -78° C., the bath was removed and the mixture was stirred at ambient temperature under a CaCl2 drying tube for 18 hours. The mixture was quenched in ice and water (500 ml) and the resulting mixture was neutralized with saturated NaHCO3 solution to pH 7. The aqueous layer was separated and evaporated to dryness in vacuo. The residue was triturated with boiling IPA and filtered hot. Evaporation of the filtrate to dryness under reduced pressure left an oil that was chromatographed on silica gel. The product was eluted with 80 CHC13 -20 CH3OH saturated with concentrated NH4OH and then triturated with CH3CN to yield 2.4 g (41%) of 43; m.p. 277° -279° C.

Workup

customthe bath was removed
customThe mixture was quenched in ice
customThe aqueous layer was separated
customevaporated to dryness in vacuo
customThe residue was triturated with boiling IPA
filtrationfiltered hot
customEvaporation of the filtrate to dryness under reduced pressure
waitleft an oil that
customwas chromatographed on silica gel
washThe product was eluted with 80 CHC13 -20 CH3OH saturated with concentrated NH4OH
customtriturated with CH3CN

Sources & evidence

ORD record: ord-ef900bc426494badb4a87730d06eb00a
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04853383

Reaction notes

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