Dichloromethane → [5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

HRID 39003

Reaction equation

HRID 39003 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]([CH2:12][OH:13])[O:7][C:6]=2[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1.[C:18]1(C)[C:19]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.[CH2:29](Cl)Cl>CN(C1C=CN=CC=1)C>[CH3:29][C:22]1[CH:23]=[CH:18][C:19]([S:24]([O:13][CH2:12][CH:8]2[O:7][C:6]3[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=[C:2]([F:1])[C:11]=3[O:10][CH2:9]2)(=[O:25])=[O:26])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 8623o-Toluenesulfonyl chlorideHCID 66879117[5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

Product 1

HCID 86652936[5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of [5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.4 g, 1.7 mmol), toluenesulfonyl chloride (0.5 g, 2.6 mmol), TEA (0.4 ml, 2.6 mmol) and 4-DMAP (0.2 g, 1.7 mmol) in DCM (10 ml) was stirred at rt for 1 h. DCM was added and the resulting mixture was washed with HCl (1 N) and brine. The organic phase was dried (Na2SO4) and evaporated to dryness to give the title compound (0.7 g). MS m/z (rel. intensity, 70 eV) 416 (M+, 31), 244 (bp), 243 (26), 231 (19), 91 (70).

Workup

  1. washthe resulting mixture was washed with HCl (1 N) and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-17a5df4cda5c49fea3146204156f6994
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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