Benzene, 1-bromo-3-nitro- → HCID 86641448, compound

HRID 1189942Notes

Reaction equation

HRID 1189942 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4].Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C(N(CC)CC)C>[F:1][C:2]([F:10])([F:9])[C:3]([NH:5][CH2:6][C:7]#[C:8][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)=[O:4]

Participants

6

Reactant 2

HCID 11457Benzene, 1-bromo-3-nitro-HCID 110948052,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide

Product 1

HCID 86641448HCID 86641448, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

2,2,2-Trifluoro-N-(prop-2-ynyl)acetamide (3.4 g, 22.2 mmol), 1-bromo-3-nitrobenzene (14) (3.0 g, 14.85 mmol), Pd(Ph3P)4 (0.85 g, 0.74 mmol) and CuI (0.14 g, 0.74 mmol) was added to triethylamine (30 mL) and the mixture was flushed with argon for 15 min. The reaction mixture was stirred at 90° C. for 16 h, cooled and diluted with ethyl acetate. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. Purification by column chromatography (100-200 silica mesh, 15% to 20% EtOAc in hexane) gave 2,2,2-trifluoro-N-(3-(3-nitrophenyl)prop-2-ynyl)acetamide as a brown semi-solid. Yield (1.95 g, 48%); 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 8.16 (d, J=8.0 Hz, 1H), 1.79 (d, J=7.6 Hz, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.34 (s, 1H), 4.38 (s, 2H).

Workup

  1. customthe mixture was flushed with argon for 15 min
  2. temperaturecooled
  3. additiondiluted with ethyl acetate
  4. filtrationThe mixture was filtered through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification by column chromatography (100-200 silica mesh, 15% to 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-8aec125056d249218464730eeede7c49
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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