Hydrochloric Acid → HCID 86086323, compound

HRID 1784538Notes

Reaction equation

HRID 1784538 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C:5]([C:14]([F:17])([F:16])[F:15])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[C:21]([Cu])#[N:22].Cl>CN1C(=O)CCC1>[N+:18]([C:3]1[CH:4]=[C:5]([C:14]([F:17])([F:16])[F:15])[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:7][C:2]=1[C:21]#[N:22])([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86086321HCID 86086321, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86086323HCID 86086323, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-bromo-2-nitro-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzene from step 2 (30.54 g, 83.0 mmol) and CuCN (7.80 g, 87.1 mmol) in NMP (83 mL) was heated to 150° C. for 30 min. Cooled to 23° C., poured into 1 N HCl, extracted with EtOAc, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a dark brown oil (33.9 g). Silica gel column chromatography with heptane/EtOAc 9:1->4:1 gave the title compound as a yellow solid (22.05 g, 85%). MS (EI) 314 [M].

Workup

  1. temperatureCooled to 23° C.
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent in vacuum
  6. waitleft a dark brown oil (33.9 g)

Sources & evidence

ORD record
ord-0e2ef43922434b4383fbb884d8e7649e
Source dataset
uspto-grants-2009_03
Patent number
US07504404B2

Reaction notes

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