Boron tribromide → HCID 86702316, compound

HRID 923823Notes

Reaction equation

HRID 923823 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:15]=1)[O:12][C:11](=[O:21])[C:10]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=1)=[CH:9]2.B(Br)(Br)Br>ClCCl>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:15]=1)[O:12][C:11](=[O:21])[C:10]([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)=[CH:9]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86702315HCID 86702315, compound

Product 1

HCID 86702316HCID 86702316, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6,8-Bis-(4-hydroxy-butyl)-3-(4-methoxy-phenyl)-chromen-2-one (14.3 g, 36.0 mmol) is dissolved in 270 ml dichloromethane and a solution of boron tribromide (12 ml, 126 mmol) in 30 ml dichloromethane is added under ice-cooling. The cooling is removed and the reaction mixture is stirred overnight at room temp. The solution is poured onto ice/water, acidified with 2 N hydrochloric acid, and extracted three times with ethyl acetate. The combined organic layers are washed with water and dried over sodium sulfate. The solvent is removed in vacuo and the residue is filtered through silica gel with toluene/THF (7:3). 6,8-Bis-(4-hydroxy-butyl)-3-(4-hydroxy-phenyl)-chromen-2-one is obtained as a viscous oil.

Workup

  1. temperaturecooling
  2. customThe cooling is removed
  3. additionThe solution is poured onto ice/water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers are washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. filtrationthe residue is filtered through silica gel with toluene/THF (7:3)

Sources & evidence

ORD record
ord-16d0f4135e20445788416891690d1525
Source dataset
uspto-grants-2016_03
Patent number
US09279082B2

Reaction notes

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