Ethylene Glycol → 7-Bromo-4-chloro-2-methyl-2,3-dihydrobenzofuran-5-carbonitrile

HRID 576351Notes

Reaction equation

HRID 576351 reaction equation
[CH2:1]([O:4][C:5]1[C:12]([Br:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7]([Cl:14])[CH:6]=1)[CH:2]=C.[CH2:15](O)CO>>[Br:13][C:12]1[C:5]2[O:4][CH:1]([CH3:2])[CH2:15][C:6]=2[C:7]([Cl:14])=[C:8]([C:9]#[N:10])[CH:11]=1

Participants

3

Reactant 2

HCID 174Ethylene GlycolHCID 867140364-(Allyloxy)-5-bromo-2-chlorobenzonitrile

Product 1

HCID 710769037-Bromo-4-chloro-2-methyl-2,3-dihydrobenzofuran-5-carbonitrileYield 52%

Procedure

The compound 38 (2.03 g, 7.45 mmol) in ethylene glycol (5 mL) was subjected to microwave conditions (Biotage®) at 250° C. for 90 min. The reaction mixture was cooled to r.t. and extracted with EtOAc/H2O (50 mL/100 mL). The organic layer was dried over MgSO4, filtered off, and evaporated in vacuo. The residue was purified using normal phase column chromatography to obtain the title product (1.05 g, 52%).

Workup

  1. extractionextracted with EtOAc/H2O (50 mL/100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered off
  4. customevaporated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-5c89b694a2994ad3bbb9f04445f8f366
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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