Diphenyl Ether → HCID 19612125, compound

HRID 1602670Notes

Reaction equation

HRID 1602670 reaction equation
Br[CH2:2][C:3]([Br:5])=[O:4].[C:6]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[O:12]([C:13]1[CH:14]=[CH:15][C:16]([CH2:2][C:3]([Br:5])=[O:4])=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19612125HCID 19612125, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 3.31 g (0.038 mol) of bromoacetyl bromide, 50 ml of methylene chloride and 5 g (0.029 mol) of diphenyl ether is cooled to 0-5° C. and 4.42 ml (0.033 mol) of aluminum chloride are added. The mixture is stirred at room temperature for 4 hours. It is poured into a-water/ice mixture, the two phases are separated and the organic phase is washed with 1 N hydrochloric acid and with water. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a silica gel column using a 7/3 cyclohexane/ethyl acetate mixture as the eluent. The fraction of the medium corresponding to 3.2 g of 2-(4-phenoxyphenyl)acetyl bromide is isolated. The resulting oil is mixed with 5.9 ml (0.077 mol) of trifluoroacetic acid and 7.7 ml (0.048 mol) of triethylsilane. The mixture is heated at 80° C. for 4 hours and the residue is taken up with an ethyl ether/sodium bicarbonate mixture. The two phases are separated, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give 7 g of the title compound.

Workup

  1. customthe two phases are separated
  2. washthe organic phase is washed with 1 N hydrochloric acid and with water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is evaporated off under reduced pressure
  5. customThe residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-233ec099a9be42b4b397d15e794a4222
Source dataset
uspto-grants-1999_11
Patent number
US05981754

Reaction notes

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