Dimethylformamide → 2-(2-Nitro-4-trifluoromethylphenoxy)-4-(1,1-dimethylpropyl)benzene

HRID 1416351Notes

Reaction equation

HRID 1416351 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9](O)=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].Br[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1[N+:24]([O-:26])=[O:25].CN(C)C=[O:30]>>[N+:24]([C:15]1[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:14]=1[O:30][C:10]1[CH:11]=[C:6]([C:2]([CH3:5])([CH3:1])[CH2:3][CH3:4])[CH:7]=[CH:8][CH:9]=1)([O-:26])=[O:25]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 66434-tert-PentylphenolHCID 5207064-Bromo-3-nitrobenzotrifluoride

Product 1

HCID 539589052-(2-Nitro-4-trifluoromethylphenoxy)-4-(1,1-dimethylpropyl)benzene

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(1,1-dimethylpropyl)phenol (821 mg, 0.005 mol), 4-bromo-3-nitrobenzotrifluoride (1.35 g, 0.005 mol) potassium carbonate (1.38 g, 0.010 mol) and cuprous oxide (143 mg, 0.001 mol) in dimethylformamide (25 ml) was stirred under argon at 150 ° C. for sixteen hours. The solvent was evaporated and the residue partitioned between ethyl acetate and water, the layers separated, dried over MgSO4 and evaporated. The crude product flash chromatographed (silica gel, ethyl acetate/hexane) to give the title compound as a yellow oil. 1H NMR (250 MHz, CDCl3) ∂ 8.20 (d, 1H), 7.70 (dd, 1H), 7.45 (m, 2H), 7.05 (m, 3H), 1.65 (q, 3H), 1.30 (s, 6H), 0.65 (t, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. customthe layers separated
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product flash chromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a1b761a532b7401aa786d2cda717fefd
Source dataset
uspto-grants-1999_06
Patent number
US05912270

Reaction notes

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