5-Fluoro-2-nitrophenol → tert-Butyl 2-(5-fluoro-2-nitrophenoxy)propylcarbamate

HRID 532255Notes

Reaction equation

HRID 532255 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].[C:12]([O:16][C:17](=[O:23])[NH:18][CH2:19][CH:20](O)[CH3:21])([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C>C1COCC1>[F:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH:6]=1)[O:11][CH:20]([CH3:21])[CH2:19][NH:18][C:17](=[O:23])[O:16][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 9920508tert-butyl N-(2-hydroxypropyl)carbamate

Product 1

HCID 58413346tert-Butyl 2-(5-fluoro-2-nitrophenoxy)propylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Nitro-5-fluorophenol (3.0 g) and tert-butyl-N-(2-hydroxypropyl)carbamate were dissolved in THF (20 ml) and triphenylphosphine (7.5 g) and di-tert-butyl-azodicarboxylate were added. The exothermic reaction was cooled in an ice bath. Then the reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and the residue was purified by chromatography (silica gel/dichloromethane: petroleum ether 1:2). The fractions were combined and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with 1M NaOH. The organic layer was separated, dried, filtered and concentrated in vacuo.

Workup

  1. customThe exothermic reaction
  2. temperaturewas cooled in an ice bath
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by chromatography (silica gel/dichloromethane: petroleum ether 1:2)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with 1M NaOH
  8. customThe organic layer was separated
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a54366de612342b5a3f8b964f31e818d
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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