Potassium Carbonate → 4-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

HRID 985045Notes

Reaction equation

HRID 985045 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2].O[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 207681224-[(4-Hydroxymethylphenyl)sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

Product 1

HCID 207681104-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

An oven-dried 500 mL round-bottomed flask was charged with crude 7.3 (prepared from 7.2 (30.0 g, 90.2 mmol)) and DMF (200 mL) and cooled to 0° C. Next, 4-hydroxybenzotrifluoride (17.5 g, 108 mmol) and K2CO3 (24.9 g, 180 mmol) were added at 0° C., and the reaction heated to 70-80° C. and stirred for 2 h. The reaction mixture was poured into ice-water (400 mL), and the product was extracted with toluene (400 mL). The organic layer was successively washed with water (2×300 mL) and brine (400 mL), dried over MgSO4, and concentrated to give a slightly yellow oil which was purified by flash chromatography (SiO2 gel 60 N, eluted with AcOEt/hexane=⅙). The fractions containing only desired product were combined and concentrated to a slightly yellow oil (40.9 g). 1H NMR (400 MHz) (CDCl3) δ 7.53 (2H, d, J=8.6 Hz); 7.30-7.20 (4H, m); 7.17 (2H, d, J=8.4 Hz); 7.00 (2H, d, J=8.7 Hz); 6.68 (1H, d, J=8.4 Hz); 5.04 (2H, s); 4.66 (2H, s); 4.27 (2H, q, J=7.1 Hz); 2.27 (3H, s); 1.30 (3H, t, J=7.1 Hz).

Workup

  1. temperaturethe reaction heated to 70-80° C.
  2. extractionthe product was extracted with toluene (400 mL)
  3. washThe organic layer was successively washed with water (2×300 mL) and brine (400 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a slightly yellow oil which
  7. customwas purified by flash chromatography (SiO2 gel 60 N, eluted with AcOEt/hexane=⅙)
  8. additionThe fractions containing only desired product
  9. concentrationconcentrated to a slightly yellow oil (40.9 g)

Sources & evidence

ORD record
ord-98dd4d8822b045049ca9d80412a434ed
Source dataset
uspto-grants-2005_03
Patent number
US06869975B2

Reaction notes

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