Trifluoroacetic acid → 4-Benzylbenzyl bromide

HRID 1857543Notes

Reaction equation

HRID 1857543 reaction equation
[C:1]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Br:14])=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(OCC)(=O)C>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][Br:14])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1229514-(Bromomethyl)benzophenone

Product 1

HCID 100382674-Benzylbenzyl bromideYield 52.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Benzoylbenzyl bromide (2.75 grams, 10.0 mmole) and triethylsilane (2.33 grams, 20 mmole) in trifluoroacetic acid (4.56 grams, 40 mmole) were warmed to 60° C. for 18 hours. The cooled mixture was diluted with ethyl acetate (50 ml) and carefully washed with saturated sodium bicarbonate solution (2×50 ml). After drying with magnesium sulfate, the extract was filtered and concentrated. The residue was chromatographed (0.5:99.5 to 2:98--ethyl acetate:hexane) to give 1.37 grams (52%) of 4-benzylbenzyl bromide as a colorless oil.

Workup

  1. washcarefully washed with saturated sodium bicarbonate solution (2×50 ml)
  2. dry with materialAfter drying with magnesium sulfate
  3. filtrationthe extract was filtered
  4. concentrationconcentrated
  5. customThe residue was chromatographed (0.5:99.5 to 2:98--ethyl acetate:hexane)

Sources & evidence

ORD record
ord-f8c78c16938846acb3539017e7330e50
Source dataset
uspto-grants-2000_11
Patent number
US06147061

Reaction notes

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