Potassium Carbonate → [3-Methyl-5-(4-trifluoromethylphenyl)thien-2-yl]methanol

HRID 2235654Notes

Reaction equation

HRID 2235654 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][OH:8])=[C:4]([CH3:9])[CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=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>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([C:2]2[S:6][C:5]([CH2:7][OH:8])=[C:4]([CH3:9])[CH:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 21986508HCID 21986508, compound

Product 1

HCID 21986444[3-Methyl-5-(4-trifluoromethylphenyl)thien-2-yl]methanolYield 48.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 62.5 (0.100 g, 0.48 mmol), 4-(trifluoromethyl)benzeneboronic acid 61.1 (0.183 g, 0.97 mmol), K2CO3 (0.200 g, 1.45 mmol), and Pd(PPh3)4 (0.056 g, 0.05 mmol) in toluene (3.2 mL) was stirred overnight at 100° C. The mixture was cooled to room temperature, filtered through a pad of silica gel (EtOAc), and concentrated. The crude product was chromatographed on silica gel (0-30% EtOAc/hexane) to afford 62.6 (0.063 g, 48%) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.66 (d, 2H), 7.61 (d, 2H), 7.14 (s, 1H), 4.79 (s, 2H), 2.27 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of silica gel (EtOAc)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-992d3e706540481abd31c86e7f5a30a9
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

Loading…