(Diethylamino)sulfur trifluoride → 3-(2-(Benzyloxy)-1-fluoroethyl)-6-bromo-2-chloropyridine

HRID 595768Notes

Reaction equation

HRID 595768 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([C:12]1[C:13]([Cl:19])=[N:14][C:15]([Br:18])=[CH:16][CH:17]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:26])CC)C>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]([C:12]1[C:13]([Cl:19])=[N:14][C:15]([Br:18])=[CH:16][CH:17]=1)[F:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 903324402-(Benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol

Product 1

HCID 903324543-(2-(Benzyloxy)-1-fluoroethyl)-6-bromo-2-chloropyridineYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol (1.54 g, 4.49 mmol) in DCM (10 mL) at 0° C. was added diethylaminosulfur trifluoride (0.594 ml, 4.49 mmol). The resulting mixture was stirred at 0° C. for 30 min, then warmed to RT and stirred for 1 h. The mixture was concentrated in vacuo and the resulting residue purified using column chromatography (eluted with 0-20% ethyl acetate/hexane) to provide 3-(2-(benzyloxy)-1-fluoroethyl)-6-bromo-2-chloropyridine (490 mg, yield: 32%)

Workup

  1. temperaturewarmed to RT
  2. stirringstirred for 1 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe resulting residue purified
  5. washcolumn chromatography (eluted with 0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d3215340dfb14d3c9b2009bdf445f9b2
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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