Benzenepropanol → (3-Fluoropropyl)benzene

HRID 605875Notes

Reaction equation

HRID 605875 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(S(F)(F)[F:17])CC)C>ClCCl>[F:17][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31234BenzenepropanolHCID 123472(Diethylamino)sulfur trifluoride

Product 1

HCID 11804828(3-Fluoropropyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Phenyl-1-propanol (1 mL) and (diethylamino)sulfur trifluoride (1.2 mL) were dissolved in dichloromethane (10 mL). The reaction solution was stirred at rt for 3 d. The reaction mixture was passed through a short silica gel column and washed with dichloromethane. The collected solution was evaporated to give 1-fluoro-3-phenylpropane as light yellow oil. 1H NMR (DMSO-d6): δ 1.84-2.02 (m, 2H), 2.65 (t, J=7.5 Hz, 2H), 4.34 (t, J=5.7 Hz, 1H), 4.50 (t, J=5.7 Hz, 1H), 7.20 (m, 5H); 19F NMR (282 MHz, DMSO-d6): δ−79.22.

Workup

  1. washwashed with dichloromethane
  2. customThe collected solution was evaporated

Sources & evidence

ORD record
ord-8f3f2911de3549c89f938a9ebc1fd80b
Source dataset
uspto-grants-2011_03
Patent number
US07915273B2

Reaction notes

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