Ammonium fluoride → HCID 25017610, compound

HRID 511983Notes

Reaction equation

HRID 511983 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][S:12](Cl)(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[F-:17]>CC(C)=O>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][S:12]([F:17])(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 25017609HCID 25017609, compound

Product 1

HCID 25017610HCID 25017610, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Phenoxybutylsulfonyl fluoride (17) was synthesized as in 13.1 using 16 (0.4 g, 1.6 mmol) and NH4F (0.118 g, 3.2 mmol) in dry acetone (20 mL). Purification by flash column chromatography on silica gel gave 17 (0.338 g, 91% yield) as a white solid (m p 74-76° C.) 1H NMR (500 MHz, CDCl3) δ 7.29 (t, J=7.5 Hz, 2H), 6.97 (t, J=7.5 Hz, 1H), 6.89 (d, J=7.5 Hz, 2H), 4.03 (t, J=5.5 Hz, 2H), 3.52-3.48 (m, 2H), 2.20 (quintet, J=7.7 Hz, 2H), 2.00 (quintet, J=8.0 Hz, 2H).

Workup

  1. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-be924b9026d14eec970a8f25bfa46314
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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