Diphenylmethane → HCID 19612141, compound

HRID 1602671Notes

Reaction equation

HRID 1602671 reaction equation
Br[CH2:2][C:3]([Br:5])=[O:4].[C:6]1([CH2:12][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>[CH2:12]([C:6]1[CH:11]=[CH:10][C:9]([CH2:2][C:3]([Br:5])=[O:4])=[CH:8][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7580DiphenylmethaneHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19612141HCID 19612141, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 2.7 g (0.030 mol) of bromoacetyl bromide, 54 ml of methylene chloride and 4 g (0.0238 mol) of diphenylmethane is cooled to 0-5° C. and 3.7 ml (0.0274 mol) of aluminum chloride are added. The mixture is stirred at room temperature for 4 hours. It is poured into a water/ice mixture and the two phases are separated. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue is taken up with isopropyl ether, the mixture is stirred and the precipitate formed is filtered off. 4.5 g of 2-(4-benzylphenyl)acetyl bromide are isolated. The resulting product is mixed with 8 ml of trifluoroacetic acid and 4.57 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 6.5 g of the title compound, which is purified by chromatography on a silica gel column using a 9/1 cyclohexane/ethyl acetate mixture as the eluent. The first eluted fraction, which corresponds to the title compound, is isolated.

Workup

  1. customthe two phases are separated
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe solvent is evaporated off under reduced pressure
  4. stirringthe mixture is stirred
  5. customthe precipitate formed
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-b4e9fec60f0b4ecd8cf24a5b55c4aa1f
Source dataset
uspto-grants-1999_11
Patent number
US05981754

Reaction notes

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