1,2-Difluorobenzene → HCID 178444405, compound

HRID 1198321Notes

Reaction equation

HRID 1198321 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].C([O-])(C)(C)C.[K+].[CH2:20]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32]I)[CH2:27][CH2:26]1)[CH2:21][CH2:22][CH2:23][CH3:24]>CCCCCC.O1CCCC1>[F:6][C:7]1[C:8]([F:13])=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:32][CH2:31][C@H:28]1[CH2:29][CH2:30][C@H:25]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 97061,2-DifluorobenzeneHCID 23665647Potassium tert-butoxideHCID 178418339ButyllithiumHCID 178444481HCID 178444481, compound

Product 1

HCID 178444405HCID 178444405, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 0.21 mol of n-butyllithium in 130 ml of hexane is added to a mixture of 0.25 mol of 1,2-difluorobenzene, 0.20 mol of potassium tert.-butanolate and 200 ml of tetrahydrofuran at -100° C. After the mixture has been stirred for 10 minutes, a mixture of 0.2 mol of 2-(trans-4-pentylcyclohexyl)-ethyl iodide, 0.2 mol of dimethylaminepropyleneurea and 50 ml of tetrahydrofuran is added at -90° C. After the mixture has been stirred at -40° C. for 1 hour, customary working up gives the ethane derivative of boiling point 135° C./0.5 mm Hg, in addition to a little 1,4-di-(2-trans-4-pentylcyclohexyl)-ethyl)-2,3-difluorobenzene as a by-product, of C 64° C. N 106.7° I.

Workup

  1. additionis added at -90° C
  2. stirringAfter the mixture has been stirred at -40° C. for 1 hour

Sources & evidence

ORD record
ord-8b251a8c940a409cbe9f99f14a4e0c82
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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