2,5-Dichloronitrobenzene → 3-(4-Chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl ester

HRID 1773525Notes

Reaction equation

HRID 1773525 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([O:14][C:15]([CH:17]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1)=[O:16])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl>[CH2:12]([O:14][C:15]([CH:17]1[CH2:21][CH2:20][CH:19]([O:22][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:18]1)=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 69772,5-DichloronitrobenzeneHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 53407781Ethyl 3-hydroxycyclopentanecarboxylate

Product 1

HCID 580562213-(4-Chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl esterYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,4-dichloro-2-nitro-benzene (190 mg, 1.1 mmol), 3-hydroxy-cyclopentanecarboxylic acid ethyl ester (180 mg, 1.14 mmol), triphenylphosphine (448 mg) and DIAD (345 mg) in dichloromethane (10 mL) was stirred at room temperature overnight. The reaction mixture was then evaporated under reduced pressure and the crude residue was purified by flash chromatography to afford 280 mg of 3-(4-chloro-2-nitro-phenoxy)-cyclopentanecarboxylic acid ethyl ester.

Workup

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. customthe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7e3ddfa5dd90428e9fce5a23ea53e54b
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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