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

HRID 609629Notes

Reaction equation

HRID 609629 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12](Cl)=[O:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[C:6]([C:12](=[O:13])[CH2:11][Cl:10])[CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 137781301-(5-Bromo-2-hydroxyphenyl)-2-chloroethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromoanisole (17.4 ml, 138 mmol) in dichloromethane (150 ml) was added chloroacetyl chloride (32 ml, 400 mmol) followed by aluminium chloride (60 g, 450 mmol) keeping the temperature below 30° C. The yellow solution was heated to reflux for 8 hours, cooled down to ambient temperature, then ice water was added very carefully. The organic layer was separated and the aqueous extracted once with dichloromethane. The combined organics were dried (sodium sulphate) then evaporated to give an oil which was purified by crystallisation from hexane. The title compound was obtained as a yellow solid (18 g, 52%), mp 80-82° C. 1H NMR (250MHz, CDCl3) δ4.69 (2H, s), 6.95 (1H, d, J=9 Hz), 7.60 (1H, dd, J=1 and 9 Hz), 7.80 (1H, d, J=2 Hz), 11.60 (1H, s).

Workup

  1. customthe temperature below 30° C
  2. temperatureThe yellow solution was heated
  3. temperatureto reflux for 8 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous extracted once with dichloromethane
  6. dry with materialThe combined organics were dried (sodium sulphate)
  7. customthen evaporated
  8. customto give an oil which
  9. customwas purified by crystallisation from hexane

Sources & evidence

ORD record
ord-9ee067a2ba3142d3b78b28ce912a5e46
Source dataset
uspto-grants-1999_12
Patent number
US05998416

Reaction notes

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