(Diethylamino)sulfur trifluoride → 1-Bromo-3-[3-(2-fluoro-ethyl)-cyclobutyl]-benzene

HRID 2240961

Reaction equation

HRID 2240961 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][CH:10]([CH2:12][CH2:13]O)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(S(F)(F)[F:21])CC)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:11][CH:10]([CH2:12][CH2:13][F:21])[CH2:9]2)[CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 593052992-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol

Product 1

HCID 593053661-Bromo-3-[3-(2-fluoro-ethyl)-cyclobutyl]-benzeneYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol (0.600 gm, 2.35 mmol) was dissolved in dichloromethane (10 mL) and chilled to −78° C. The solution was treated with (diethylamino)sulfur trifluoride (468 mg, 2.88 mmol) and monitored by TLC. The crude reaction was poured onto silica and purified by column chromatography (10% EtOAc in hexanes) to afford 250 mg of an oil (41%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.79 (m, 2H) 1.83-2.09 (m, 2H) 2.14-2.34 (m, 2H) 2.37-2.44 (m, 1H) 3.27-3.63 (m, 1H) 4.27-4.52 (m, 2H) 7.16-7.24 (m, 2H) 7.29-7.40 (m, 2H); MS (EI) m/z 256 [M+·].

Workup

  1. customThe crude reaction
  2. additionwas poured onto silica
  3. custompurified by column chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d5a48b9f8b2142d9b3688473e655c3a4
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Linked notes

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