Bromotrimethylsilane → 2-Phenyl-2-bromododecane

HRID 241464Notes

Reaction equation

HRID 241464 reaction equation
[CH3:1][C:2](O)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C[Si]([Br:24])(C)C>ClCCl.CCOCC>[C:13]1([C:2]([Br:24])([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:1])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 651476661-Methyl-1-phenylundecyl alcohol

Product 1

HCID 670844072-Phenyl-2-bromododecane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

10.50 g (0.04 mol) of 1-methyl-1-phenylundecyl alcohol was dissolved in 50 ml of dichloromethane, cooled in ice bath, 10.6 ml (12.29 g, 0.08 mol) of trimethylsilyl bromide was added and the mixture stirred for 1 h under protection from moisture. The solution was diluted with 100 ml ether and washed four times with 50 ml water, brine, dried and evaporated to give crude 2-phenyl-2-bromododecane. 35 ml of 2.3 M hydrogen peroxide in THF (0.08 mol) was added to the 2-phenyl-2-dodecyl bromide and the mixture was cooled on ice bath. 8.84 g (0.04 mol) of silver trifluoroacetate was added. 70 ml of conc. NaHCO3 was added and the mixture filtered. The reaction flask and the filter cake was rinsed with diethyl ether. The aqueous phase was separated and the organic phase washed with conc. NaHCO3, 50 ml water, brine, dried and evaporated to give an oil. The oil was purified by flash chromatography using 2:8 ether:pentane as eluent. The yield of 1-methyl-1-phenylundecyl hydroperoxide was 30%.

Workup

  1. temperaturecooled in ice bath
  2. washwashed four times with 50 ml water, brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-353b196a4df24c2a8236354132292d09
Source dataset
uspto-grants-2014_02
Patent number
US08650742B2

Reaction notes

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