Bromine → 2-bromo-1-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]ethanone

HRID 238686Notes

Reaction equation

HRID 238686 reaction equation
[C:1]1([C@@H:7]2[O:11][N:10]=[C:9]([C:12]([C:14](=O)C)=[O:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17]Br>ClCCCl.ClC(Cl)C.O>[Br:17][CH2:14][C:12]([C:9]1[CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:11][N:10]=1)=[O:13]

Participants

6

Reactant 2

HCID 24408BromineHCID 687444941-[(5R)-4,5-dihydro-5-phenyl-3-isoxazoyl]ethanone

Product 1

HCID 866312472-bromo-1-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]ethanoneYield 72.9%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
30 °C

Procedure

1-[(5R)-4,5-dihydro-5-phenyl-3-isoxazoyl]ethanone (3.2 g, 16.7 mmol) was dissolved in 1,2-dichloroethane (15 mL), and a solution of bromine (2.13 g, 13.3 mmol) in dichloroethane (5 mL) was added over 30 minutes while maintaining the temperature of the reaction mixture at about 30° C. The reaction mixture was diluted with water (10 mL), and the organic layer was concentrated under reduced pressure and purified by medium-pressure liquid chromatography using 35% of dichloromethane in hexanes as eluant to give 2.6 g of the title compound as a white solid, melting at 31-33° C.

Workup

  1. concentrationthe organic layer was concentrated under reduced pressure
  2. custompurified by medium-pressure liquid chromatography

Sources & evidence

ORD record
ord-c4ae47e3f13644f9b97dab5773755906
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Reaction notes

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