O-Cresol → 2-[4-(Trifluoromethyl)benzyloxy]toluene

HRID 1991147Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.O>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([C:16]([F:15])([F:25])[F:26])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methylphenol (12.53 g, 115.9 mmol) was dissolved in DMF (60 mL), and stirred at 0° C. To the solution was added K2CO3 (24.03 g, 173.9 mmol) and 4-trifluoromethylbenzyl bromide (23.08 g, 96.6 mmol), and the reaction was stirred at room temperature for 2 h. Water was added to the reaction, and the product was extracted with EtOAc twice. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo to give a crude residue. The crude residue was purified using silica gel column chromatography (hexane/EtOAc=30/1) to give 4.1 (25.1 g). 1H NMR (400 MHz) (CDCl3) δ 7.64 (2H, d, J=8.2 Hz); 7.56 (2H, d, J=8.2 Hz); 7.18-7.08 (2H, m); 6.90 (1H, t, J=7.2 Hz); 6.84 (1H, d, J=8.1 Hz); 5.14 (2H, s); 2.30 (3H, s).

Workup

stirringthe reaction was stirred at room temperature for 2 h
extractionthe product was extracted with EtOAc twice
washThe organic layer was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customto give a crude residue
customThe crude residue was purified

Sources & evidence

ORD record: ord-677552d421434f579cd46942fd425de6
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645779B2

Reaction notes

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