Boron tribromide → HCID 66596773, compound

HRID 504008Notes

Reaction equation

HRID 504008 reaction equation
B(Br)(Br)Br.[C:5]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:21]3[C:16](=[C:17]([O:28]C)[CH:18]=[CH:19][C:20]=3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:15][CH2:14][C:13]2=[O:30])=[CH:7][CH:6]=1>ClCCl>[C:5]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[CH:7][C:8]([CH2:11][N:12]2[C:21]3[C:16](=[C:17]([OH:28])[CH:18]=[CH:19][C:20]=3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:15][CH2:14][C:13]2=[O:30])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66596881HCID 66596881, compound

Product 1

HCID 66596773HCID 66596773, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (12 ml) of 2N boron tribromide was added dropwise at −20° C. to a dichloromethane solution (50 ml) of 1-(biphenyl-4-ylmethyl)-5-methoxy-8-phenyl-3,4-dihydro-1H-quinolin-2-one (5.00 g). After stirring for 4 hours, the reaction mixture was poured into ice water and separated into layers. The organic layer was washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from a dichloromethane-diisopropyl ether mixed solvent to thereby obtain 5.01 g (yield: quantitative) of 1-(biphenyl-4-ylmethyl)-5-hydroxy-8-phenyl-3,4-dihydro-1H-quinolin-2-one as a white powder.

Workup

  1. customseparated into layers
  2. washThe organic layer was washed twice with water
  3. washwashed with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from a dichloromethane-diisopropyl ether mixed solvent

Sources & evidence

ORD record
ord-c745db33a8fe42a5a77a9627c6e3a1a9
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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