Boron tribromide → HCID 15407850, compound

HRID 2393515Notes

Reaction equation

HRID 2393515 reaction equation
B(Br)(Br)Br.[OH:5][C:6]1[CH:7]=[C:8]2[CH:25]=[CH:24][CH:23]=[CH:22][C:9]2=[C:10]2[C:19]=1[O:18][C:17]1[C:12](=[CH:13][C:14]([O:20]C)=[CH:15][CH:16]=1)[O:11]2>ClCCl>[OH:5][C:6]1[CH:7]=[C:8]2[CH:25]=[CH:24][CH:23]=[CH:22][C:9]2=[C:10]2[C:19]=1[O:18][C:17]1[C:12](=[CH:13][C:14]([OH:20])=[CH:15][CH:16]=1)[O:11]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15407849HCID 15407849, compound

Product 1

HCID 15407850HCID 15407850, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an inert atmosphere, 0.1 ml of boron tribromide is added dropwise to 90 mg of 6-hydroxy-10-methoxy-7,12-dioxabenz[a]anthracene in solution in 3 ml of dichloromethane at 0° C. After 4 hours, the mixture is hydrolyzed. The organic phase is dried over magnesium sulfate and concentrated under vacuum. The bis-hydroxylated compound is purified by flash chromatography on silica gel (eluent: petroleum ether/ethyl acetate).

Workup

  1. dry with materialThe organic phase is dried over magnesium sulfate
  2. concentrationconcentrated under vacuum
  3. customThe bis-hydroxylated compound is purified by flash chromatography on silica gel (eluent: petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-1dc34cf6b6504983aeef9a002cd6c41a
Source dataset
uspto-grants-1998_09
Patent number
US05807882

Reaction notes

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