Water → 4-Ethynyl-4'-pentyl-1,1'-biphenyl

HRID 370669Notes

Reaction equation

HRID 370669 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.C([Li])CCC.O>O1CCCC1.CCCCCC>[C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[CH:2]

Participants

6

Reactant 3

HCID 962WaterHCID 202749594-(2,2-Dibromovinyl)-4'-pentylbiphenylHCID 178418339Butyllithium

Product 1

HCID 34468404-Ethynyl-4'-pentyl-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

In an analogous manner to Example 1, solution of 4-(2,2-dibromovinyl)-4'-pentylbiphenyl in absolute tetrahydrofuran was placed in a sulphonation flask and treated within 5 minutes with a solution of butyl lithium in hexane. After completion of the addition, the mixture was warmed to -10° C. within 10 minutes, then poured into water and extracted with diethyl ether. The organic phases were washed with water and saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography of the residue on silica gel with hexane and recrystallization from methanol gave 4-ethynyl-4'-pentylbiphenyl as colourless crystals (purity 99.5%); m.p. (C-N) 56.4° C., cl.p. (N-I) 82.7° C.

Workup

  1. additionAfter completion of the addition
  2. extractionextracted with diethyl ether
  3. washThe organic phases were washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customLow-pressure chromatography of the residue on silica gel with hexane and recrystallization from methanol

Sources & evidence

ORD record
ord-3e60a6c94eb24f9b835c75eb0571c829
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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