p-Chlorophenacyl bromide → HCID 44232240, compound

HRID 414916Notes

Reaction equation

HRID 414916 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[O:3]1.Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=O.C(=O)([O-])O.[Na+]>C(O)CC>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[N:15]=[C:12]3[CH:11]=[CH:10][C:9]([B:4]4[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]4)=[CH:14][N:13]3[CH:18]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 68303p-Chlorophenacyl bromideHCID 516892Sodium BicarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 44232240HCID 44232240, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

2.5 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine and 2.65 g of 2-bromo-1-(4-chlorophenyl)ethanone in 76 ml of n-propanol are placed in a round-bottomed flask. 1.33 g of sodium hydrogen carbonate are added thereto. The mixture is heated at 80° C. for 16 h. The reaction mixture is left to cool and concentrated under reduced pressure. The residue is taken up between water and ethyl acetate, the organic phase is then separated by settling out and dried over magnesium sulphate, and the solvent is then evaporated off under reduced pressure. 3.75 g of compound are obtained.

Workup

  1. waitThe reaction mixture is left
  2. temperatureto cool
  3. concentrationconcentrated under reduced pressure
  4. customthe organic phase is then separated
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record
ord-4b1cf724c7db4818a9c81626cff341bc
Source dataset
uspto-grants-2012_01
Patent number
US08088765B2

Reaction notes

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