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

HRID 963979

反応式

HRID 963979 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 122234581,1-Diphenyl-4-bromobutane収率 72.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15294c53c5684764a7b2f8ffc4894105
出典データセット
uspto-grants-1998_06
特許番号
US05767129

関連ノート

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