Trichloroacetyl chloride → HCID 57517331, compound

HRID 1629719Notes

Reaction equation

HRID 1629719 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8])[CH:2]=[CH2:3].C(N(CC)CC)C.[Cl:20][C:21]([Cl:26])([Cl:25])[C:22](Cl)=[O:23]>ClCCl>[Cl:20][C:21]([Cl:26])([Cl:25])[C:22]([O:12][C:11]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[CH2:1][CH:2]=[CH2:3])=[O:23]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 2584423-Allyl-4-hydroxybenzonitrile

Product 1

HCID 57517331HCID 57517331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of INT 25 (10.0 g, 62.8 mmol) in dichoromethane (450 mL) was added triethylamine (7.98 g, 79 mmol), followed by dropwise addition of trichloroacetyl chloride (14.42 g, 79 mmol) and the resulting mixture was stirred at room temperature overnight. The mixture was washed with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated to give INT 26 which was used in the next step without further purification.

Workup

  1. washThe mixture was washed with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give INT 26 which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c7ee30a34e4c4f0593cf33a4f1b69252
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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