5-Fluoro-2-nitrophenol → HCID 58421788, compound

HRID 406002Notes

Reaction equation

HRID 406002 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([OH:20])[CH:19]=1.[CH:24]1(O)[CH2:29][CH2:28][CH2:27][CH:26]=[CH:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH:29]1([O:20][C:18]2[CH:19]=[C:14]([F:13])[CH:15]=[CH:16][C:17]=2[N+:21]([O-:23])=[O:22])[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]1

Participants

6

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 131982-Cyclohexen-1-OLHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 58421788HCID 58421788, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.89 ml DEAD were added to an ice-cooled solution of the 1.57 g 5-Fluoro-2-nitrophenol, 1.18 ml 2-cyclohexenol and 3.15 g triphenylphosphin in methylene chloride. The reaction mixture was stirred and allowed to warm to rt overnight. The solvent was removed in vacuo. Purification is achieved by silica gel column chromatography with iso-hexane/EtOAc (gradient: 100% i-hexane→10:1 i-hexane/EtOAc).

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-b58ae56b7e444246a825b6b9b9427c89
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

Loading…