4-Toluenesulfonyl chloride → HCID 18411857, compound

HRID 2240581Notes

Reaction equation

HRID 2240581 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][OH:30].[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][O:30][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Product 1

HCID 18411857HCID 18411857, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.02 g of p-toluensulfonyl chloride (5.35 mM), 1.24 ml of diisopropyl ethylamine (7.13 mM) and 86 mg of 4-(dimethylamino)pyridine (0.71 mM) were added to the reaction solution (3.57 mM) containing 500 mg of 2-(2-fluoro-phenyl)-ethanol (3.57 mM) dissolved in methylene chloride solution with stirring for 6 hrs at 0° C. under Ar atmosphere, and then the reaction mixture was stirred for 12 hrs at room temperature. The resulting mixture was neutralized with ammonium chloride, extracted with ethyl acetate and washed with saturated NaCl solution to separate into an organic layer and water layer. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:7) as an eluant to give 740 mg of toluen-4-sulfonate-2-(2-fluoro-phenyl)-ethyl ester (u) (yield: 70%).

Workup

  1. stirringthe reaction mixture was stirred for 12 hrs at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated NaCl solution
  4. customto separate into an organic layer and water layer
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant was purified by Silica gel column chromatography with a solvent mixture
  9. additionmixed with methanol and chloroform (1:7) as an eluant

Sources & evidence

ORD record
ord-31286ab4509f47199cce0f14ac02eeda
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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