Carbon Tetrachloride → 5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

HRID 8236

Reaction equation

HRID 8236 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11]O)=[CH:10][C:4]=2[O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:34]>>[Cl:34][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[O:6][C:2]([F:13])([F:1])[O:3][C:4]=2[CH:10]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Product 1

HCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

Conditions

Temperature
80 °C

Procedure

A solution of (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (1.0 g, 5.32 mmol) in carbon tetrachloride (10.6 mL) is added to polymer-supported triphenylphospine (3.5 g, 3 mmol/g, 10.6 mmol) at room temperature. The reaction is heated for 3 h at 80° C., cooled to room temperature, filtered, and the solids washed with dichloromethane. The filtrate is concentrated in vacuo to yield the title compound, 0.79 g (72%), as a clear, orange oil.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washthe solids washed with dichloromethane
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f65978114b994b5ead93e25904dd8fe7
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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