Hydrochloric Acid → HCID 53417938, compound

HRID 900845Notes

Reaction equation

HRID 900845 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[Cu][C:17]#[N:18].Cl>CN1CCCC1=O>[CH3:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]([N+:13]([O-:15])=[O:14])=[C:2]([CH:7]=1)[C:17]#[N:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 534071971-Bromo-5-methyl-2-nitro-4-(trifluoromethyl)benzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 53417938HCID 53417938, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-bromo-5-methyl-2-nitro-4-trifluoromethyl-benzene from step 2 (49.80 g, 175 mmol) and copper(I) cyanide (16.5 g, 184 mmol) in 1-methyl-2-pyrrolidone (NMP) (180 mL) was heated up to 150° C. and stirred for 30 min under nitrogen atmosphere. The mixture was cooled to 23° C. and poured into 1 N HCl, extracted with TBME, washed with brine and dried over Na2SO4. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel column chromatography with heptane/ethyl acetate 4:1->2:1 to give the title compound as a light yellow solid (35.48 g, 88%). MS (EI) 230.1 [M].

Workup

  1. temperatureThe mixture was cooled 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, which
  7. customwas purified by silica gel column chromatography with heptane/ethyl acetate 4

Sources & evidence

ORD record
ord-0d492660eb9d414aa1127a4c2237e92e
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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