Acetate → 2-Nitro-5-(3-trifluoromethylphenoxy)-m-xylene

HRID 2181585Notes

Reaction equation

HRID 2181585 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C([O-])(=O)C.C(N(CC)CC)C>ClCCl.[Cu]>[N+:8]([C:7]1[C:2]([CH3:1])=[CH:3][C:4]([O:12][C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:14]([F:25])([F:24])[F:13])[CH:20]=2)=[CH:5][C:6]=1[CH3:11])([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 175AcetateHCID 8471TriethylamineHCID 1384663,5-Dimethyl-4-nitrophenolHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 224812122-Nitro-5-(3-trifluoromethylphenoxy)-m-xylene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,5-dimethyl-4-nitrophenol (1.67 g), 3-trifluoromethylbenzene boronic acid (3.8 g), copper (1 acetate (1.82 g) and triethylamine (2.02 g) in dichloromethane (50 ml) was stirred at room temperature for 48 hours. The mixture was evaporated to dryness and purified by silica gel chromatography eluting with light petroleum (b.p. 60-80° C.)/ethyl acetate (19:1) to give the title product as an oil.

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified by silica gel chromatography
  3. washeluting with light petroleum (b.p. 60-80° C.)/ethyl acetate (19:1)

Sources & evidence

ORD record
ord-229927daf8a64ea6baf6ee8059966bb0
Source dataset
uspto-grants-2005_05
Patent number
US06893650B1

Reaction notes

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