Thionyl Chloride → HCID 118308888, compound

HRID 1481991Notes

Reaction equation

HRID 1481991 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13]O)[CH2:2][CH:3]=[CH2:4].S(Cl)([Cl:17])=O>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13][Cl:17])[CH2:2][CH:3]=[CH2:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 103616254HCID 103616254, compound

Product 1

HCID 118308888HCID 118308888, compoundYield 91%

Procedure

(2-(But-3-en-1-yloxy)-5-fluorophenyl)methanol (6.3 g, 32.1 mmol, 1 equiv) was taken up in thionyl chloride (107 mL) and heated to reflux for 1 h. Upon cooling to ambient temperature, the solution was concentrated in vacuo. The residue was concentrated in vacuo with benzene (×3) to remove residual thionyl chloride and provide the benzyl chloride (6.3 g, 91%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.12 (dd, J=8.7, 3.1 Hz, 1H), 6.98 (ddd, J=8.9, 8.0, 3.1 Hz, 1H), 6.82 (dd, J=9.0, 4.3 Hz, 1H), 5.93 (ddt, J=17.1, 10.3, 6.8 Hz, 1H), 5.25-5.09 (m, 2H), 4.62 (s, 2H), 4.05 (t, J=6.5 Hz, 2H), 2.58 (qt, J=6.6, 1.3 Hz, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. concentrationthe solution was concentrated in vacuo
  4. concentrationThe residue was concentrated in vacuo with benzene (×3)
  5. customto remove residual thionyl chloride

Sources & evidence

ORD record
ord-b7ba7250ca764e208ab5fa7727423939
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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