Dicyclohexylcarbodiimide → HCID 19103571, compound

HRID 1198323Notes

Reaction equation

HRID 1198323 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].FC1C=C(O)C=CC=1C#N.C(Br)CCC.C(=O)([O-])[O-].[K+].[K+].CN(C1C=CC=CN=1)C.[F:46][C:47]1[C:52]([F:53])=[C:51]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH:50]=[CH:49][C:48]=1O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:48]1[CH:49]=[CH:50][C:51]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])=[C:52]([F:53])[C:47]=1[F:46])=[O:5]

Participants

9

Reactant 6

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 27734344-butoxy-2-fluorobenzoic acidHCID 144956302,3-Difluoro-4-octylphenolHCID 86747516HCID 86747516, compound

Product 1

HCID 19103571HCID 19103571, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.1 mol of 2-fluoro-4-butyloxybenzoic acid (prepared from 3-fluoro-4-cyanophenol by alkylation with butyl bromide/potassium carbonate in dimethylformamide and subsequent hydrolysis of the nitrile via the imido ester), 0.01 mol of dimethylaminopyridine and 0.1 mol of 2,3-difluoro-4-octylphenol are initially introduced into 150 ml of methylene chloride, a solution of 0.1 mol of dicyclohexylcarbodiimide in 30 ml of methylene chloride is added dropwise at 10°, while stirring, and the mixture is then subsequently stirred at room temperature for 15 hours. The mixture is filtered over silica gel and the solvent is evaporated to give 2,3-difluoro-4-octylphenyl 2-fluoro-4-butyloxybenzoate as the residue.

Workup

  1. stirringthe mixture is then subsequently stirred at room temperature for 15 hours
  2. filtrationThe mixture is filtered over silica gel
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-72f8c0cb865949ab9d7c8822f601ff6b
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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