Water → HCID 67015589, compound

HRID 1617612Notes

Reaction equation

HRID 1617612 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.B(Br)(Br)Br.O.C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 67015565HCID 67015565, compound

Product 1

HCID 67015589HCID 67015589, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 3-(4-bromo-phenyl)-1-(4-methoxy-phenyl)-3-o-tolyl-propan-1-one (214 mg) in dichloromethane (5.1 ml) under argon was cooled to −78° C. A solution of BBr3 (2.09 ml, 1 M in dichloromethane) was added dropwise. The mixture was stirred at −78° C. for 45 min, at 0° C. for 4 h and at room temperature for 30 min. Since the reaction was not complete, the mixture was again cooled to −78° C. and a solution of BBr3 (1 ml, 1 M in dichloromethane) was added. The mixture was stirred at −78° C. for 30 min and at 0° C. for 4.5 h. Water and a saturated aqueous NaHCO3 solution were added and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried using MgSO4, filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 7:3) to give the title compound (21 mg) as a light brown solid, MS (ESI+): m/z=394.8 [M−H]−.

Workup

  1. temperaturethe mixture was again cooled to −78° C.
  2. stirringThe mixture was stirred at −78° C. for 30 min and at 0° C. for 4.5 h
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic phase was washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 7:3)

Sources & evidence

ORD record
ord-7b8d4007f94349e9bc9eeaa44a3ab973
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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