Propargyl bromide → HCID 60681748, compound

HRID 1260336Notes

Reaction equation

HRID 1260336 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]2[O:6][C:7]([F:10])([F:9])[O:8][C:4]=2[CH:3]=1.[CH2:13](Br)[C:14]#[CH:15]>C1(C)C=CC=CC=1>[F:9][C:7]1([F:10])[O:6][C:5]2[CH:11]=[CH:12][C:2]([NH:1][CH2:15][C:14]#[CH:13])=[CH:3][C:4]=2[O:8]1

Participants

4

Reactant 2

HCID 7842Propargyl bromideHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxole

Product 1

HCID 60681748HCID 60681748, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-amino-2,2-difluorobenzo-1,3-dioxole (2.8 g, 16.17 mmol) in 25 mL of anhydrous toluene was dropwise added propargyl bromide (0.99 mL, 11 mmol). The mixture was heated to 80° C. overnight after which it was allowed to cool to ambient temperature and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography using DCM as eluant to provide the titled compound. 1H NMR (CDCl3) δ ppm 2.22 (1H), 3.85 (2H), 6.30-6.85 (3H); MS (ESI) 212 (M+H).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-86004ebbdf38424a92433a8c48cec115
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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