Cyclopentanol → 4-Bromo-1-(cyclopentyloxy)-2-nitrobenzene

HRID 646173Notes

Reaction equation

HRID 646173 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12]1(O)[CH2:16][CH2:15][CH2:14][CH2:13]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 243644-Bromo-2-nitrophenolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 613758734-Bromo-1-(cyclopentyloxy)-2-nitrobenzeneYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-bromo-2-nitrophenol (1.0 g, 4.6 mmol), cyclopentanol (600 mg, 7.0 mmol) and Ph3P (1.47 g, 5.6 mmol) in THF (50 mL) at 0° C. was portion-wise added diisopropylazodicarboxylate (1.52 g, 7.5 mmol) in THF (10 mL) and the resulting mixture was left to stir overnight at ambient temperature. Solvent removal and purification by chromatography on silica gel afforded the sub-title compound (1.24 g, 94%).

Workup

  1. waitthe resulting mixture was left
  2. customSolvent removal and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-61f2c25840554e998c3a381be422dfef
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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