4-Toluenesulfonyl chloride → 2-(2-Fluoroethoxy)ethyl 4-methylbenzenesulfonate

HRID 2403752Notes

Reaction equation

HRID 2403752 reaction equation
[F:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][F:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 97632-(2-Fluoroethoxy)ethan-1-ol

Product 1

HCID 595577772-(2-Fluoroethoxy)ethyl 4-methylbenzenesulfonateYield 27%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(2-Fluoroethoxy)ethanol (0.11 g, 1.0 mmol), p-toluenesulfonyl chloride (0.19 g, 1.0 mmol), and DMAP (0.12 g, 1.0 mmol) were dissolved in dichloromethane (2 ml) at 0° C. The resulting mixture was stirred for 2 h at 0° C., after which it was subjected directly to silica gel chromatography using dichloromethane as the eluent to give the title compound (70 mg, 27%) as a clear oil. It was observed that the size of the column affects reaction yield, with a smaller column giving a better yield. 1H NMR (CDCl3, 300 MHz): δ 7.79 (d, 2H, J=11.6 Hz), 7.33 (d, 2H, J=11.6 Hz), 4.48 (dt, 2H, J1=64.0 Hz, J2=5.6 Hz), 4.17 (t, 2H, J=6.4 Hz), 3.71 (t, 2H, J=6.4 Hz), 3.66 (dt, 2H, J1=5.6 Hz, J2=39.2 Hz), 2.44 (br S, 3H).

Sources & evidence

ORD record
ord-fcdffa1d1bd84611889e226b40de8394
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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