Bromine → HCID 19784796, compound

HRID 2081890Notes

Reaction equation

HRID 2081890 reaction equation
[Br:1]Br.[F:3][C:4]([F:17])([F:16])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]>C(O)(=O)C>[F:3][C:4]([F:16])([F:17])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:1])=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 19784794HCID 19784794, compound

Product 1

HCID 19784796HCID 19784796, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (2.33 ml, 2 eq.) in acetic acid (15 ml) was added dropwise to a stirred solution of N-(2,2,2-trifluoroethyl)-2-nitroaniline (4) (5.0 g, 23 mmol) inacetic acid (50 ml), in an ice bath. After the bromine addition was completed, the ice bath was removed and the reaction mixture was stirred at room temperature for 30 minutes and poured onto crushed ice. The resultant yellow-orange precipitate was collected by filtration, washed with H2O three times and air dried to give 6.0 g (88% yield) of N-(2,2,2,-trifluoroethyl)-4-bromo-2-nitroaniline (5): mp 118°-120° C.; MS m/e 298 (M+), 1HNMR (DMSO-d6) δ 4.33 (m, 2H), 7.28 (d, 1H, J=9.0 Hz), 7.72 (dd, 1H, J=2.2 Hz, 9.0 Hz), 8.18 (d, 1H, J=2.1 Hz), 8.31 (1H, -NH).

Workup

  1. customthe ice bath was removed
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe resultant yellow-orange precipitate was collected by filtration
  5. washwashed with H2O three times and air
  6. customdried

Sources & evidence

ORD record
ord-1912524e64de497a888fd68c37a859af
Source dataset
uspto-grants-1993_02
Patent number
US05186716

Reaction notes

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