4-Toluenesulfonyl chloride → 3-Fluoroprop-1-yl toluene-4-sulphonate

HRID 599192Notes

Reaction equation

ClCCCO.[F-].[K+].[F:8][CH2:9][CH2:10][CH2:11][OH:12].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C(O)CO.N1C=CC=CC=1.[Na+].[I-]>[CH3:20][C:19]1[CH:21]=[CH:22][C:16]([S:13]([O:12][CH2:11][CH2:10][CH2:9][F:8])(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 3-chloropropanol (2.5 mL, 30 mmol), KF (3.5 g, 60 mmol) and NaI (50 mg, 0.33 mmol) in ethylene glycol (10 mL) was placed in a round-bottom flask attached to a short-path distillation condenser. The mixture was heated at 130° C. and the resulting 3-fluoropropanol was collected as a colorless liquid. To a 0° C. solution of 3-fluoropropanol (600 mg, 7.68 mmol) in pyridine (8 mL) was added tosyl chloride (3.2 g, 16.78 mmol) over 30 min. The reaction mixture was stirred at 0° C. for 4 h and quenched by adding ice-cold water and EtOAc. The product fluorotosylate was purified as described in Method 14 above to afford compound 21 (1.2 g, 67%) as a slightly yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=10.0 Hz, 1H), 7.38 (d, J=10.0 Hz, 2H), 4.59 (dt, J=50.0 & 5.0 Hz, 2H), 4.28 (dt, J=30.0 & 5.0 Hz, 2H), 2.47 (s, 3H).

Workup

customwas placed in a round-bottom flask
customattached to a short-path distillation condenser
customthe resulting 3-fluoropropanol was collected as a colorless liquid
customquenched
additionby adding ice-cold water and EtOAc
customThe product fluorotosylate was purified

Sources & evidence

ORD record: ord-b5d0c8b808a1487b9e42ecb657bcd48a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897769B2

Reaction notes

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