p-Toluenesulfonic acid → HCID 19103502, compound

HRID 1198334Notes

Reaction equation

HRID 1198334 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[O:14][CH2:15][CH3:16].[CH3:17]N(CCN(C)C)C.[C:25]1(C)[CH:30]=[CH:29][C:28](S(O)(=O)=O)=[CH:27][CH:26]=1.[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1COCC1.C1(C)C=CC=CC=1>[CH2:15]([O:14][C:8]1[CH:9]=[CH:10][C:11]([C:3]([C:2]2[CH:1]=[CH:17][C:38]([C:39]3[CH:30]=[CH:25][C:26]([CH2:27][CH2:28][CH3:29])=[CH:41][CH:40]=3)=[CH:37][CH:36]=2)=[CH2:4])=[C:12]([F:13])[C:7]=1[F:6])[CH3:16]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 27829281-Ethoxy-2,3-DifluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 19103502HCID 19103502, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

66 ml of a 1.6N solution of butyllithium in n-hexane are added dropwise to a solution of 0.1 mol of 2,3-difluorophenetole and 0.1 mol of TMEDA in 200 ml of THF at -70° C. After stirring for 4 hours at -70° C. 0.1 mol of 4-acetyl-4'-propylbiphenyle in 50 ml of THF are added. After customary working up the product and 2 g of p-toluenesulfonic acid are dissolved in 200 ml of toluene and the mixtung is heated under reflux for 0.5 hours. Working up gives 1-(4-ethoxy-2,3-difluorphenyl)-1-(4'-propylbiphenyl-4-yl)-ethene.

Workup

  1. temperaturethe mixtung is heated
  2. temperatureunder reflux for 0.5 hours

Sources & evidence

ORD record
ord-da8af42da2924c5d9cd76648d268cba9
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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