5-Fluoro-2-nitrophenol → cis-4-Fluoro-2-(2-methoxy-cyclohexyloxy)-1-nitro-benzene

HRID 406020Notes

Reaction equation

HRID 406020 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.[CH3:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)Cl>[F:13][C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([O:20][C@@H:27]2[CH2:28][CH2:29][CH2:30][CH2:31][C@@H:26]2[O:25][CH3:24])[CH:19]=1

Participants

7

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 102911Cyclohexanol, 2-methoxy-HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 67382391cis-4-Fluoro-2-(2-methoxy-cyclohexyloxy)-1-nitro-benzene

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.36 ml DEAD were added to an ice-cooled solution of the 1.57 g 5-fluoro-2-nitrophenol, 1.95 ml 2-methoxycyclohexanol and 3.93 g triphenylphosphine in 30 ml THF. The reaction mixture was allowed to warm to rt overnight. The mixture was stirred additional 48 hours. Then the reaction mixture was diluted with methylene chloride and washed with 10% aq. potassium carbonate solution. The organic phase was passed through a hydrophobic frit and evaporated. Purification was achieved by silica gel column chromatography (solvent:10:1 iso-hexane: EtOAc).

Workup

  1. washwashed with 10% aq. potassium carbonate solution
  2. customevaporated
  3. customPurification

Sources & evidence

ORD record
ord-427f75dbc9b24be0a9dd8076790ea3f4
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

Loading…