Hydrogen Bromide → HCID 22998022, compound

HRID 52309Notes

Reaction equation

HRID 52309 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](Cl)=[CH2:9])=[CH:4][CH:3]=1.BrN1[C:18](=O)[CH2:17][CH2:16][C:15]1=O.[BrH:21].[C:22](#N)[CH3:23].[OH2:25]>CCOCC>[Br:21][CH2:22][C:23](=[O:25])[CH2:9][C:8]1[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=1[O:6][C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 122548641-(4-Chlorophenoxy)-2-chloro-2-propeneHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 22998022HCID 22998022, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a turbid solution of 1-(4-chlorophenoxy)-2-chloro-2-propene from Step 1 (3 g, 15.7 mmol) in acetonitrile/water (4/1, 100 mL), N-bromosuccinimide (4.84 g, 31.4 mmol) was added in one lot. A catalytic amount of 48% HBr (40 μl) was added to the reaction and the yellowish orange mixture was stirred at room temperature. After 24 hours, the reaction mixture was diluted with ether and washed with 5% w/v of sodium thiosulfate. The organic layer was separated and washed with saturated sodium bicarbonate and brine. After drying (MgSO4), filtration and concentration in vacuo, the crude liquid (4.8 g) was chromatographed (silica gel, hexane/ethyl acetate, 80/20) to give crude 1-bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone (2.3 g, 54%) which was used in the next step without further purification.

Workup

  1. washwashed with 5% w/v of sodium thiosulfate
  2. customThe organic layer was separated
  3. washwashed with saturated sodium bicarbonate and brine
  4. customAfter drying
  5. filtration(MgSO4), filtration and concentration in vacuo
  6. customthe crude liquid (4.8 g) was chromatographed (silica gel, hexane/ethyl acetate, 80/20)

Sources & evidence

ORD record
ord-385fb46f10b44196a89d41e35fbede4c
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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