1-Propanol → 2-Fluoro-1-nitro-4-propoxybenzene

HRID 1594517Notes

Reaction equation

HRID 1594517 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:12](O)[CH2:13][CH3:14].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>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 10311-PropanolHCID 11776TriphenylphosphineHCID 5209483-Fluoro-4-nitrophenolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 684297512-Fluoro-1-nitro-4-propoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 3-fluoro-4-nitrophenol (32 mmol, 5.0 g), 1-propanol (48 mmol, 3.9 mL), and triphenylphosphine (64 mmol, 16.8 g) in CH2Cl2 (160 mL) at 0° C. was added DIAD (64 mmol, 12 mg). The reaction mixture was concentrated in vacuo. The product was isolated by flash chromatography on silica eluting with 5% EtOAc in hexanes. H1 NMR (500 MHz, CDCl3): δ 8.13 (t, J=8.7 Hz, 1H), 6.81-6.75 (m, 2H), 4.05 (d, J=6.4 Hz, 2H), 1.90 (m, 2H), 1.10 (t, J=7.3 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe product was isolated by flash chromatography on silica eluting with 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-6aca2258445440f19de348de9c3b3def
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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