Bromine → HCID 53935881, compound

HRID 1417561Notes

Reaction equation

HRID 1417561 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([CH3:15])=[O:14])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[Br:16]Br.S([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([Br:16])[C:13]([CH3:15])=[O:14])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 54282318HCID 54282318, compound

Product 1

HCID 53935881HCID 53935881, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 100 mg (0.369 mmol) of 1-(3-bromo-4-isopropoxyphenyl)acetone (from Example 228, Step C) in toluene (0.26 mL) was added bromine (0.019 mL, 0.369 mmol) dropwise via syringe. After stirring 30 min. At RT, a solution of sodium sulfite (676 mg) in water (1.5 mL)) was added and the mixture was extracted with 3×15 mL of ethyl ether. The combined organic layers were washed 20 mL of saturated sodium bicarbonate followed by 20 mL of brine. Drying over sodium sulfate and evaporation gave 119 mg of product as a red oil. Mass spectrum (NH3/CI): m/z=349 (M+1)

Workup

  1. extractionthe mixture was extracted with 3×15 mL of ethyl ether
  2. washThe combined organic layers were washed 20 mL of saturated sodium bicarbonate
  3. dry with materialDrying over sodium sulfate and evaporation

Sources & evidence

ORD record
ord-ad65ca5819f3460fb0b8b21c53dcb2e9
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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