Hydrogen Bromide → HCID 67000344, compound

HRID 1042756Notes

Reaction equation

HRID 1042756 reaction equation
Br.[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[O:22][CH2:21][CH2:20][C:19]4=[O:26])[CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:29][CH2:30][CH2:31][O:32][CH3:33]>CC(O)C>[BrH:2].[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[O:22][CH2:21][CH2:20][C:19]4=[O:26])[CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:29][CH2:30][CH2:31][O:32][CH3:33]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 44182694HCID 44182694, compound

Product 1

HCID 67000344HCID 67000344, compoundYield 136.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 48% aqueous hydrobromic acid solution (170 μL, 2.4 mmol) was added with ice cooling to a solution of the compound (1.00 g, 2.00 mmol) obtained in Example 3 in 2-propanol (10 mL), and the solution was warmed to room temperature and stirred overnight. The resulting precipitate was collected by filtration, then washed with 2-propanol (1 mL×2), and then dried under reduced pressure to obtain a crude crystal of the title compound (797 mg). The crude crystal (750 mg) was added to 2-propanol (30 mL), and the mixture was heated under reflux. The dissolution of the solid matter was confirmed. The solution was then gradually cooled to room temperature, while it was stirred for 19 hours. The resulting precipitate was collected by filtration, then washed with 2-propanol (1 mL×2), and then dried under reduced pressure to obtain the title compound (613 mg) as a white crystalline solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with 2-propanol (1 mL×2)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-a675a36490db46ea9ef24628831d7d39
Source dataset
uspto-grants-2013_10
Patent number
US08557998B2

Reaction notes

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