Hydrogen Bromide → HCID 22998022, compound

HRID 1166325Notes

Reaction equation

HRID 1166325 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 purified by chromatography (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 purified by chromatography (silica gel, hexane/ethyl acetate, 80/20)

Sources & evidence

ORD record
ord-9006e5bdd1a5497ca8e591aa2237dcd7
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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