2,4,4,6-Tetrabromocyclohexa-2,5-dienone → 4-Bromo-2-methoxy-3-(trifluoromethyl)aniline

HRID 751070

Reaction equation

HRID 751070 reaction equation
[CH3:1][O:2][C:3]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[Br:14]C1C(=O)C(Br)=CC(Br)(Br)C=1>C(Cl)Cl>[Br:14][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[C:9]=1[C:10]([F:11])([F:12])[F:13]

Participants

4

Reactant 2

HCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone2×HCID 201120252-Methoxy-3-(trifluoromethyl)aniline

Product 1

HCID 597543364-Bromo-2-methoxy-3-(trifluoromethyl)anilineYield 16.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 17C (200 mg, 1.05 mmol) in CH2Cl2 (2 mL) cooled to −20° C. was added dropwise a solution of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (429 mg, 1.05 mmol) in CH2Cl2 (2 mL). After the addition, the reaction was stirred at rt overnight, then additional amount of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (429 mg, 1.05 mmol) was added. The reaction was continued for 2 more days, then concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 10%-20% EtOAc/hexane to yield the title compound (47mg, 16% yield).

Workup

  1. additionAfter the addition
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed (silica gel)
  4. washeluting with 10%-20% EtOAc/hexane

Sources & evidence

ORD record
ord-a4af7da20749495d8a968de84b6517b6
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Linked notes

Loading…