Sodium Hydroxide → Phenol, 2-chloro-4-fluoro-5-nitro-

HRID 2060702Notes

Reaction equation

HRID 2060702 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[Cl:13].[OH-].[Na+]>O>[Cl:13][C:4]1[CH:5]=[C:6]([F:12])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[OH:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 37866902-Chloro-4-fluoro-5-nitrophenyl methyl carbonate

Product 1

HCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-Yield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-4-fluoro-5-nitrophenyl methyl carbonate (120 g 0.48 mol) was combined with a solution of sodium hydroxide (22.7 g, 0.57 mol) in water (300 mL) and the resultant mixture was refluxed for 4 h. The insoluble solids were removed by filtration and the filtrate was acidified with dilute HCl. The precipitated solid was collected by filtration and washed with water to give 2-chloro-4-fluoro-5-nitrophenol (90 g, 98% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.18 (s, 1H), 8.10 (d, J=10.4 Hz, 1H), 7.62 (d, J=7.2 Hz, 1H); MS (ESI) m/z: 192.1 (M+H+).

Workup

  1. customThe insoluble solids were removed by filtration
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-a4d45a87b4d2466f8b1566b69da0b41b
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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