2-Bromo-5-nitroanisole → 2-Bromo-5-nitrophenol

HRID 383408Notes

Reaction equation

HRID 383408 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[O:26]C.Cl.N1C=CC=CC=1>>[N+:9]([C:7]1[CH:6]=[CH:5][C:4]([C:12]([F:13])([F:14])[F:15])=[C:3]([OH:2])[CH:8]=1)([O-:11])=[O:10].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[OH:26]

Participants

5

Reactant 3

HCID 1012932-Bromo-5-nitroanisoleHCID 10176127Pyridinium chlorideHCID 177559612-Methoxy-4-nitro-1-(trifluoromethyl)benzene

Product 2

HCID 128671362-Bromo-5-nitrophenolHCID 219595865-Nitro-2-(trifluoromethyl)phenol

Conditions

Temperature
210 °C

Procedure

To a mixture of 2-methoxy-4-nitro-1-(trifluoromethyl)benzene and 1-bromo-2-methoxy-4-nitro-benzene (16 g, crude) was added pyridine hydrochloride (100 g, 860 mmol) and the reaction mixture was stirred at 210° C. for 40 min. Then the mixture was poured into ice-water and extracted with EtOAc (80 mL×3). The combined organic layers were washed with water (100 mL×2) and brine (50 mL), dried over anhydrous Na2SO4 and purified by silica gel column chromatography (5% EtOAc in petroleum as eluant) to afford 5-nitro-2-(trifluoromethyl)phenol and 2-bromo-5-nitrophenol (10 g, crude). 1H-NMR (300 MHz, CDCl3) δ 7.86-7.80 (m, 3H), 7.72-7.63 (m, 3H).

Workup

  1. extractionextracted with EtOAc (80 mL×3)
  2. washThe combined organic layers were washed with water (100 mL×2) and brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. custompurified by silica gel column chromatography (5% EtOAc in petroleum as eluant)

Sources & evidence

ORD record
ord-9eb20e1f08a04defa0c2213cb69d21e4
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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