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

HRID 2188861Notes

Reaction equation

HRID 2188861 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-eec0fbf64c0b4faea4a79ceff2c31871
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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