Ammonia → 4-Fluoro-2-methyl-5-nitrophenol

HRID 2064134Notes

Reaction equation

HRID 2064134 reaction equation
C(=O)(OC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([F:12])=[CH:5][C:4]=1[CH3:13].N.CO>>[F:12][C:6]1[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]([OH:2])=[C:4]([CH3:13])[CH:5]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 144216192-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

Product 1

HCID 108210594-Fluoro-2-methyl-5-nitrophenolYield 72%

Procedure

4-Fluoro-2-methyl-5-nitrophenyl methyl carbonate (D15) (2.36 mmol, 540 mg) was treated under argon with 6 mL of a 2M solution of ammonia in methanol (12 mmol NH3, 5 eq) and was allowed to stir for 1.5 h. The mixture was concentrated under reduced pressure and purified by chromatography (0-25% ethyl acetate/petrol ether) to give the title compound as bright yellow solid (1.7 mmol, 290 mg, 72% yield). M−H=170.12, Rt 2.34 min, 1H NMR δ (CDCl3) 7.48 (1H, d), 7.06 (1H, d), 5.15 (1H, s), 2.32 (3H, s).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by chromatography (0-25% ethyl acetate/petrol ether)

Sources & evidence

ORD record
ord-5cdb86c0f2fd4daa97b1cacee4ccb698
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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