Bromine → 4-Bromo-2-methoxy-6-nitroaniline

HRID 539156

Reaction equation

HRID 539156 reaction equation
CC([O-])=O.[Na+].[Br:6]Br.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:11]=1[NH2:19]>CC(O)=O>[Br:6][C:14]1[CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:11]([NH2:19])=[C:10]([O:9][CH3:8])[CH:15]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 854916-Nitro-o-anisidineHCID 517045Sodium Acetate

Product 1

HCID 508790564-Bromo-2-methoxy-6-nitroanilineYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

NaOAc (17.6 g) and Br2 (6.76 mL) was added to a solution of 2-methoxy-6-nitrobenzenamine (21.74 g) in HOAc (250 mL). The mixture was stirred at room temperature for 20 min. The resulting precipitate was filtered, washed with water and dried in-vacuo to afford the desired product as a yellow solid (26.43 g, 83%). 1H NMR (300 MHz, DMSO-d6) δ 3.91 (s, 3H), 7.18 (d, 1H, J=1.8 Hz), 7.70 (d, 1H, J=1.8 Hz); LC-MS: m/e=247 [M+1]+

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried in-vacuo

Sources & evidence

ORD record
ord-206c0df0fa68472791b9cf18403b90b8
Source dataset
uspto-grants-2014_10
Patent number
US08865912B2

Linked notes

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