3,4-Dichlorophenol → 5-(3,4-Dichloro-phenoxy)-2-nitro-4-trifluoromethyl-phenylamine

HRID 538131Notes

Reaction equation

HRID 538131 reaction equation
Cl[C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Cl:22][C:23]1[CH:24]=[C:25]([OH:30])[CH:26]=[CH:27][C:28]=1[Cl:29]>CC(N(C)C)=O>[Cl:22][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:28]=1[Cl:29])[O:30][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 27738135-Chloro-2-nitro-4-(trifluoromethyl)aniline

Product 1

HCID 669374555-(3,4-Dichloro-phenoxy)-2-nitro-4-trifluoromethyl-phenylamineYield 99%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-chloro-2-nitro-4-trifluoromethyl-phenylamine (1.00 g, 4.16 mmol) and DMA (21 mL) was added K2CO3 (1.15 g, 8.32 mmol) and 3,4-dichloro-phenol (1.36 g, 8.32 mmol). The mixture was heated to 85° C. for 18 h. The mixture was cooled to 23° C. and poured into ice water. The precipitate was collected, dissolved in EtOAc (150 mL) and washed with brine (2×30 mL). The organic layers were combined, dried, filtered, and concentrated under reduced pressure to yield the titled compound (1.51 g, 99%). 1H NMR (500 MHz, CDCl3): 8.52 (s, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.26 (d, J=3.2 Hz, 1H), 7.00 (dd, J=8.7, 2.7 Hz, 1H), 6.37 (s, 2H), 6.06 (s, 1H).

Workup

  1. temperatureThe mixture was cooled to 23° C.
  2. customThe precipitate was collected
  3. dissolutiondissolved in EtOAc (150 mL)
  4. washwashed with brine (2×30 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2f109bb9a9c4801b9c19e1baac875f7
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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