Water → 1-Bromo-3-(p-biphenylyl)-1,2-butadiene

HRID 616414

반응식

HRID 616414 반응식
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](O)([CH3:10])[C:8]#[CH:9].[Br-:18].[NH4+].O>Br>[Br:18][CH:9]=[C:8]=[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:10]

참가 물질

5

반응물 3

HCID 962WaterHCID 25514Ammonium BromideHCID 867348962-(p-Biphenylyl)-3-butyn-2-ol

생성물 1

HCID 888129191-Bromo-3-(p-biphenylyl)-1,2-butadiene

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

실험 절차

A suspension of 1.1 g of 3-(p-biphenylyl)-but-1-yn-3-ol (obtainable analogously to Steps A and B, Example 10), 1.8 g of ammonium bromide and 0.2 g cuprous chloride in 10 ml of 48% hydrobromic acid is stirred for 4 hours at room temperature. The reaction mixture is then poured into water and extracted 3 times with 8 ml portions of methylene chloride. The combined organic extracts are washed 3 times with water, dried over anh. S.S., filtered and evaporated (i.v.) to dryness to obtain a residue. The residue is chromatographed on silica gel using chloroform/pentane (1:1) as eluent. The solvent is removed by evaporation to obtain a residue, from which 1-bromo-3-(p-biphenylyl)-1,2-butadiene is crystallized from pentane.

후처리

  1. extractionextracted 3 times with 8 ml portions of methylene chloride
  2. washThe combined organic extracts are washed 3 times with water
  3. customdried over anh. S.S
  4. filtration, filtered
  5. customevaporated (i.v.) to dryness
  6. customto obtain a residue
  7. customThe residue is chromatographed on silica gel
  8. customThe solvent is removed by evaporation
  9. customto obtain a residue
  10. customfrom which 1-bromo-3-(p-biphenylyl)-1,2-butadiene is crystallized from pentane

출처 및 근거

ORD 기록
ord-cccc379850da446e894ef25cd6d2ae3d
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04073936

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