Hydrochloric Acid → HCID 66650497, compound

HRID 900852Notes

Reaction equation

HRID 900852 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[C:18]([Cu])#[N:19].Cl>CN1C(=O)CCC1>[CH2:9]([O:8][C:6]1[C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]([N+:15]([O-:17])=[O:16])=[C:2]([CH:7]=1)[C:18]#[N:19])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66650317HCID 66650317, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 66650497HCID 66650497, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-bromo-5-ethoxy-2-nitro-4-trifluoromethyl-benzene from step 2 (61.81 g, 197 mmol) and CuCN (18.51 g, 207 mmol) in NMP (197 mL) was heated to 150° C. for 30 min. Cooled to 23° C., poured into 1 N HCl, extracted with TBME, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown oil. Silica gel column chromatography with heptane/EtOAc 4:1 gave the title compound as a yellow solid (46.73 g, 91%). MS (EI) 260.1 [M].

Workup

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

Sources & evidence

ORD record
ord-4ee399c111e4422db1eab039dba681a2
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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