3-Chloro-[1,1'-biphenyl]-2-carboxaldehyde → 3-Chloro-2-ethenyl-1,1'-biphenyl

HRID 1065568Notes

Reaction equation

HRID 1065568 reaction equation
[CH2:1]([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]=1[CH:19]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.C(OCC)C>[Cl:6][C:7]1[C:8]([CH:19]=[CH2:1])=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 132166793-Chloro-[1,1'-biphenyl]-2-carboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 128530513-Chloro-2-ethenyl-1,1'-biphenylYield 53.6%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a dry argon atmosphere n-butyllithium (1.3 g, 0.020 mole) was added slowly to a stirred ice cold mixture of (methyl)triphenylphosphonium bromide (7.3 g, 0.0203 mole) in 30 ml of tetrahydrofuran. The mixture was warmed to room temperature, stirred for two hours, and 3-chloro-[1,1'-biphenyl]-2-carboxaldehyde (4.4 g, 0.0203 mole) in 30 ml of tetrahydrofuran added. The reaction mixture was stirred at room temperature for approximately 18 hours, heated at reflux for two hours, then cooled. The reaction mixture was diluted with 300 ml of diethyl ether and washed with 100 ml of water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a residue. Distillation of the residue at 88°/0.05 mm gave 3-chloro-2-ethenyl-[1,1'-biphenyl] (2.3 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for approximately 18 hours
  2. temperatureheated
  3. temperatureat reflux for two hours
  4. temperaturecooled
  5. washwashed with 100 ml of water
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a residue
  10. distillationDistillation of the residue at 88°/0.05 mm

Sources & evidence

ORD record
ord-206a8df6760440f38cc4ce9e5934d9fc
Source dataset
uspto-grants-1982_05
Patent number
US04329518

Reaction notes

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