N-methyl-2-pyrrolidone → 1,2-Dimethyl-4-(pentafluoroethyl)benzene

HRID 1408498Notes

Reaction equation

HRID 1408498 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([CH3:8])=[CH:6][CH:7]=1.[F:10][C:11]([F:19])([F:18])[C:12]([F:17])([F:16])C(O)=O.[Na].CN1CCCC1=O>[Cu]I.CCCCCC>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]([F:17])([F:16])[C:11]([F:19])([F:18])[F:10])=[CH:3][C:4]=1[CH3:9]

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 1416464-Iodo-1,2-dimethylbenzeneHCID 71650614378-77-8

Product 1

HCID 716561311,2-Dimethyl-4-(pentafluoroethyl)benzene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8058HexaneSolvent

Conditions

Temperature
170 °C

Procedure

Into a nitrogen purged, flame dried round bottom flask was added 4-iodo-o-xylene (15.0 g, 64.7 mmol), sodium pentafluoropropionic acid (16.8 g, 90.5 mmol), copper (I) iodide (12.3 g, 64.6 mmol) and 100 mL of anhydrous N-methylpyrrolidinone. The reaction mixture was heated at 170° C. for 16 hours, then cooled to room temperature, and run through a thick silica gel plug with hexane. The collected yellow liquids were then evaporated to dryness on a rotary evaporator, and the oil distilled at 60° C. (10−1 Torr) to collect the desired product (9.14 g, 63%) as a colorless liquid. Analysis of the product provided the following data: 1H NMR (200 MHz, CDCl3) δ=2.347 (s, 6H), 7.247 (d, J=7.8 Hz, 1H), 7.357 (s, 1H), 7.401 (s, 1H). 13C NMR (50 MHz, CDCl3) δ=19.810, 19.840, 124.013 (t, J=6.1 Hz), 127.472 (t, J=6.1 Hz), 130.158, 137.563, 141.205. GC-MS: m/z: 224 (C10H9F5).

Workup

  1. customInto a nitrogen purged
  2. temperatureflame
  3. customdried round bottom flask
  4. temperaturecooled to room temperature
  5. customThe collected yellow liquids were then evaporated to dryness on a rotary evaporator
  6. distillationthe oil distilled at 60° C. (10−1 Torr)
  7. customto collect the desired product (9.14 g, 63%) as a colorless liquid
  8. customAnalysis of the product provided the following data

Sources & evidence

ORD record
ord-f7fdd849f53f457e88d65317cd75a56b
Source dataset
uspto-grants-2014_12
Patent number
US08920679B2

Reaction notes

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