Bromine → HCID 19784796, compound

HRID 257243Notes

Reaction equation

HRID 257243 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 AcidSolvent2×

Procedure

Bromine (2.33 ml, 2 eq.) in acetic acid (15 ml) was added dropwise to a stirred solution of N-(2,2,2-trifluoro- ethyl)-2-nitroaniline (4) (5.0g, 23 mmol) in acetic acid (50 ml), in an ice bath. After the bromine addition was completed, the i-ce 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) δ4.33 (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 i-ce 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-6e42d26024c249a69e384c32359ac96a
Source dataset
uspto-grants-1993_11
Patent number
US05260488

Reaction notes

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