Chloroacetyl chloride → 1-(5-Bromo-2-hydroxyphenyl)-2-chloroethanone

HRID 1948680Notes

Reaction equation

HRID 1948680 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][CH:7]=1.[Cl:14][CH2:15][C:16](Cl)=[O:17]>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[C:10]([C:16](=[O:17])[CH2:15][Cl:14])[CH:11]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 77304-BromoanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137781301-(5-Bromo-2-hydroxyphenyl)-2-chloroethanoneYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

35.3 g (264.6 mmol) of aluminium trichloride are added in portions to a solution of 10 ml (80.2 mmol) of 4-bromoanisole and 18.5 ml (232.6 mmol) of chloroacetyl chloride in 90 ml of methylene chloride at a temperature less than 30° C., and the resultant reaction mixture is heated under reflux for six hours. 100 ml of ice-water are subsequently carefully added to the reaction mixture with ice-cooling, the organic phase is separated, the aqueous phase is washed twice with 50 ml of methylene chloride each time, the combined organic phases are then washed with 50 ml of water and dried over sodium sulfate. Filtering-off of the desiccant and stripping-off of the solvent gives 11.7 g of 1-(5-bromo-2-hydroxyphenyl)-2-chloroethanone as beige solid; m.p. 79° C. (lit. m.p. 80-82° C.).

Workup

  1. customthe resultant reaction mixture
  2. temperatureis heated
  3. temperatureunder reflux for six hours
  4. temperaturecooling
  5. customthe organic phase is separated
  6. washthe aqueous phase is washed twice with 50 ml of methylene chloride each time
  7. washthe combined organic phases are then washed with 50 ml of water
  8. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-01c5cc87d2cb4d98bb13178a7728c689
Source dataset
uspto-grants-2013_03
Patent number
US08399509B2

Reaction notes

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