1,2-Difluorobenzene → HCID 19746966, compound

HRID 484320Notes

Reaction equation

HRID 484320 reaction equation
[F:1][C:2]1[CH:7]=[CH:6]C=C[C:3]=1[F:8].[CH2:9]([Li])[CH2:10][CH2:11]C.[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[K+].[K].C(Br)CCCC.CN1CCCN(C)C1=O>O1CCCC1>[F:8][CH:3]([CH:2]([F:1])[CH2:7][CH3:6])[CH2:14][C:15]1[CH:18]=[CH:11][CH:10]=[CH:9][CH:16]=1

Participants

7

Reactant 5

HCID 97061,2-DifluorobenzeneHCID 5462222PotassiumHCID 23665647Potassium tert-butoxideHCID 131718030HCID 131718030, compoundHCID 178418339Butyllithium

Product 1

HCID 19746966HCID 19746966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3-Difluoro-4-pentylbenzoic acid is obtained by reacting o-difluorobenzene with butyllithium in the presence of potassium tertiary-butoxide at -90° to -100° in tetrahydrofuran, alkylating the potassium compound formed using pentyl bromide/1,3-dimethyltetrahydro-2-(1H)-pyrimidinone (DMPU), isolating the 2,3-difluoropentylbenzene, re-metallating by means of butyllithium and subsequently reacting with solid carbon dioxide. Esterification of this acid using trans-4-pentylcyclohexanol gives trans-4-pentylcyclohexyl 2,3-difluoro-4-pentylbenzoate.

Workup

  1. customat -90° to -100°
  2. customformed

Sources & evidence

ORD record
ord-bef288c7fb9a4444852b9ac737a0a8fa
Source dataset
uspto-grants-1993_07
Patent number
US05230827

Reaction notes

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