4-Toluenesulfonyl chloride → HCID 24805800, compound

HRID 715123Notes

Reaction equation

HRID 715123 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:7][CH2:6][C:3]2([C:2]([F:9])([F:8])[F:1])[CH2:5][CH2:4]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 509906611-(Trifluoromethyl)cyclopropanemethanol

Product 1

HCID 24805800HCID 24805800, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (1-(trifluoromethyl)cyclopropyl)methanol (7 g, 50 mmol) and p-toluenesulfonyl chloride (10.4 g, 55 mmol) in DCM (100 mL) with TEA (10 g, 100 mmol) and 4-dimethylaminopyridine (DMAP) (0.6 g, 5 mmol) and stir at RT overnight. Wash successively with 2 M HCl, satd. NaHCO3, and brine, dry over Na2SO4 and concentrate to give the title compound (12 g, 81%). 1H NMR (400 MHz, DMSO-d6): δ 7.79 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 2H), 4.13 (s, 2H), 2.43 (s, 3H), 1.08-1.05 (m, 2H), 0.96-0.94 (m, 2H).

Workup

  1. washWash successively with 2 M HCl
  2. dry with materialNaHCO3, and brine, dry over Na2SO4
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-3d50716c93a645c3847fa61acfd53e40
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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