Water → 2-bromo-4-nitro-6-(trifluoromethyl)aniline

HRID 1820127Notes

Reaction equation

HRID 1820127 reaction equation
[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:7]=1)([O-:5])=[O:4].O>C(O)(=O)C>[Br:1][C:10]1[CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[C:8]([C:13]([F:14])([F:15])[F:16])[C:9]=1[NH2:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidine

Product 1

HCID 114716542-bromo-4-nitro-6-(trifluoromethyl)anilineYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
120 °C

Procedure

Bromine (0.60 mL) dissolved in acetic acid (11 mL) was added dropwise to a solution of 4-nitro-2-trifluoromethyl-phenylamine (2.4 g) in acetic acid (12 mL). The reaction mixture was heated to 120° C. for 2½ hours, poured into water (400 mL) and filtered. The collected solid was washed with water (200 mL) and dried in vacuo to furnish 3.03 g (91% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6): 7.08 (s, 2H), 8.23 (d, 1H), 8.51 (d, 1H).

Workup

  1. filtrationfiltered
  2. washThe collected solid was washed with water (200 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e310d090fe264c3798ee859e489b2c15
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

Loading…