Thionyl Chloride → 4H-1,3-Benzodioxin, 6-(chloromethyl)-2,2,4,4-tetrafluoro-

HRID 401550Notes

Reaction equation

HRID 401550 reaction equation
[F:1][C:2]1([F:16])[O:7][C:6]([F:9])([F:8])[C:5]2[CH:10]=[C:11]([CH2:14]O)[CH:12]=[CH:13][C:4]=2[O:3]1.S(Cl)([Cl:19])=O>>[Cl:19][CH2:14][C:11]1[CH:12]=[CH:13][C:4]2[O:3][C:2]([F:16])([F:1])[O:7][C:6]([F:9])([F:8])[C:5]=2[CH:10]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 591662914H-1,3-Benzodioxin-6-methanol, 2,2,4,4-tetrafluoro-

Product 1

HCID 591658634H-1,3-Benzodioxin, 6-(chloromethyl)-2,2,4,4-tetrafluoro-

Procedure

A mixture of (2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxin-6-yl)-methanol (6.5 g) in thionyl chloride (75 mL) was heated at reflux overnight. The resulting mixture was concentrated under vacuum. The residue was basified with aqueous saturated NaHCO3. The aqueous layer was extracted with dichloromethane (50 mL×3). The combined organic layers were dried over Na2SO4, filtrated, and concentrated under reduced pressure to give 6-chloromethyl-2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine (6.2 g), which was used directly in the next step. 1H NMR (CDCl3, 300 MHz) δ 7.65 (s, 1H), 7.61 (dd, J=2.1, 8.7 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 4.60 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. extractionThe aqueous layer was extracted with dichloromethane (50 mL×3)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5a624abee6a40a683cc01a46187ad4b
Source dataset
uspto-grants-2014_06
Patent number
US08741933B2

Reaction notes

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