Acetic Acid → HCID 47444577, compound

HRID 528838Notes

Reaction equation

HRID 528838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CC(O)=O.[Br:24]Br.OS([O-])=O.[Na+]>O>[Br:24][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:10])[CH2:12][CH2:13]2

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 24408BromineHCID 673639ST005495HCID 23665763Sodium Bisulfite

Product 1

HCID 47444577HCID 47444577, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (3,4-dichlorophenyl)(indolin-1-yl)methanone (2.6 g, 8.90 mmol) in AcOH (8.2 mL, 142 mmol) was added bromine (504 μL, 9.79 mmol) dropwise via syringe at 0° C. Additional AcOH (6.0 mL) was added, and the reaction mixture was stirred at room temperature for 1 h. Cold water was added to the reaction mixture followed by sat. aq. NaHSO3 solution. The resulting mixture was stirred for 10 min, and the precipitate was collected via filtration to give the title compound (3.30 g, 100%) as a light brown solid. 1H NMR (DMSO-d6) δ 7.90 (d, J=1.5 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.49 (s, 1H), 7.38 (br s, 1H), 4.02 (t, J=8.3 Hz, 2H), 3.10 (t, J=8.3 Hz, 2H); MS(ESI+) m/z 371.9 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred for 10 min
  2. filtrationthe precipitate was collected via filtration

Sources & evidence

ORD record
ord-898096eac7dc43d6a717c0de67241ed0
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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