Dimethyl Sulfoxide → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

HRID 529996Notes

Reaction equation

HRID 529996 reaction equation
Cl[CH2:2][C:3]1[CH:13]=[CH:12][C:6]2[O:7][C:8]([F:11])([F:10])[O:9][C:5]=2[CH:4]=1.[C-]#N.[Na+].CS(C)=[O:19]>>[F:10][C:8]1([F:11])[O:7][C:6]2[CH:12]=[CH:13][C:3]([CH2:2][OH:19])=[CH:4][C:5]=2[O:9]1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

Product 1

HCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanolYield 66%

Conditions

Temperature
25 °C

Procedure

A mixture of 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole (117.6 g, crude from last step) and NaCN (84 g, 1.7 mmol) in DMSO (800 mL) was stirred for 2 h at 25° C. The reaction, mixture was poured into ice and extracted with EtOAc (500 mL×3). The combined organic layers were dried with anhydrous Na2SO4 and concentrated in vacuo to give crude product which was purified by column chromatography (P.E./EtOAc 10:1) to give (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol (77.8 g, 66%), 1H NMR (300 MHz , CDCl3) δ 7.06-7.07 (m, 3H), 3.75 (s, 2H).

Workup

  1. customThe reaction, mixture
  2. additionwas poured into ice
  3. extractionextracted with EtOAc (500 mL×3)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give crude product which
  7. customwas purified by column chromatography (P.E./EtOAc 10:1)

Sources & evidence

ORD record
ord-0797a945373d4257bdd5704f2c6fa036
Source dataset
uspto-grants-2016_05
Patent number
US09351962B2

Reaction notes

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