Potassium Carbonate → HCID 86725584, compound

HRID 514461Notes

Reaction equation

HRID 514461 reaction equation
CC1C=CC(S(O[CH2:12][C:13]([F:16])([F:15])[F:14])(=O)=O)=CC=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:25][OH:26])=[C:22]([OH:24])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:25][OH:26])=[C:22]([O:24][CH2:12][C:13]([F:16])([F:15])[F:14])[CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 86725584HCID 86725584, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Charged 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (1.62 g, 6.37 mmol), 5-chloro-2-(hydroxymethyl)phenol (1.01 g, 6.37 mmol, PREPARATION 7), K2CO3 (1.76 g, 12.74 mmol) and DMF (7 mL) to a flask; heated to 100° C. overnight. The reaction mixture was then poured into ice-water and extracted with EA twice, washed the organic phase with water twice, brine and dried with Na2SO4, concentrated for gel chromatograph to give the title compound (200 mg, 13%). 1H NMR (400 MHz, CDCl3): δ 4.39 (2H, q, J=8.0 Hz), 4.70 (2H, d, J=5.2 Hz), 6.83 (1H, d, J=1.6 Hz), 7.05 (1H, dd, J=1.6 Hz, 8.0 Hz), 7.33 (1H, d, J=7.6 Hz).

Workup

  1. extractionextracted with EA twice
  2. washwashed the organic phase with water twice
  3. dry with materialbrine and dried with Na2SO4
  4. concentrationconcentrated for gel chromatograph

Sources & evidence

ORD record
ord-f03524fee5f74327b99cfc0b9337679f
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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