Dimethyl Sulfoxide → 1,1-Diphenyl-4-bromobutane

HRID 963979Notes

Reaction equation

HRID 963979 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CS(C)=O>CCOCC>[Br:19][CH2:10][CH2:9][CH2:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 925194,4-Diphenylbutan-1-ol

Product 1

HCID 122234581,1-Diphenyl-4-bromobutaneYield 72.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

4,4-Diphenyl-1-butanol (22.41 g, 0.099 mol) was dissolved in ether (250 mL). CBr4 (41.07 g, 0.123 mol) was added and the reaction cooled to 0° C. Triphenylphosphine (38.96 g, 0.148 mol) in ether (400 mL) was added dropwise to the reaction. The reaction was then allowed to warm to room temperature overnight. DMSO (3.51 mL) was added, and the reaction allowed to stir for 8 hours. The white precipitate was filtered and washed with ether (100 mL). The ether was removed in vacuo, and the residue washed with hexanes and filter. The hexanes were removed in vacuo, and the residue chromatographed on silica gel eluting with hexanes to give 20.72 g (72%) of desired product as an oil.

Workup

  1. temperatureto warm to room temperature overnight
  2. filtrationThe white precipitate was filtered
  3. washwashed with ether (100 mL)
  4. customThe ether was removed in vacuo
  5. washthe residue washed with hexanes
  6. filtrationfilter
  7. customThe hexanes were removed in vacuo
  8. customthe residue chromatographed on silica gel eluting with hexanes

Sources & evidence

ORD record
ord-15294c53c5684764a7b2f8ffc4894105
Source dataset
uspto-grants-1998_06
Patent number
US05767129

Reaction notes

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