Acetonitrile → HCID 67958681, compound

HRID 1484658Notes

Reaction equation

HRID 1484658 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[Br:12])(=[O:3])[CH3:2].C(#N)C.Br[CH2:17][C:18]([CH3:20])=[CH2:19]>>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:19][C:18]([CH3:20])=[CH2:17])[C:6]=1[Br:12])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 3577853-Bromo-2-methyl-1-propeneHCID 679581882-Bromo-3-hydroxyphenyl acetate2×

Product 1

HCID 67958681HCID 67958681, compoundYield 62.2%

Procedure

To a solution of 2-bromo-3-hydroxyphenyl acetate (Intermediate 38, 3028 mg) in acetonitrile (60 ml) potassium carbonate (3623 mg, 26.2 mmol) and 3-bromo-2-methyl-1-propene (2123 mg, 15.73 mmol) were added. The reaction mixture was stirred at room temperature overnight. The mixture was washed with water (3 times 60 ml). The organic phase was separated, dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using a 100 g-SNAP column and cyclohexane/ethyl acetate from 100/0 to 80/20 as eluent to afford the title compound as a colourless oil (2.324 g).

Workup

  1. washThe mixture was washed with water (3 times 60 ml)
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel using a 100 g-SNAP column and cyclohexane/ethyl acetate from 100/0 to 80/20 as eluent

Sources & evidence

ORD record
ord-337690cf88284852b7586c75bb2c5444
Source dataset
uspto-grants-2016_08
Patent number
US09422272B2

Reaction notes

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