Hydrogen Bromide → HCID 67000344, compound

HRID 1518104Notes

Reaction equation

HRID 1518104 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-6f183e81001b4445a78725b6ed8439b3
Source dataset
uspto-grants-2012_07
Patent number
US08232405B2

Reaction notes

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