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

HRID 1584101Notes

Reaction equation

HRID 1584101 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-e47de7e057e442608b92dbdeb688a01b
Source dataset
uspto-grants-1999_08
Patent number
US05932573

Reaction notes

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