Boron tribromide → HCID 56651008, compound

HRID 1191307Notes

Reaction equation

HRID 1191307 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[C:14]4[CH:22]=[CH:21][CH:20]=[CH:19][C:15]4=[CH:16][CH:17]=3)[NH:12][C:11](=[O:23])[N:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[C:14]4[CH:22]=[CH:21][CH:20]=[CH:19][C:15]4=[CH:16][CH:17]=3)[NH:12][C:11](=[O:23])[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 56651007HCID 56651007, compound

Product 1

HCID 56651008HCID 56651008, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold suspension of 4-(3-methoxyphenyl)-1H-benzo[h]quinazolin-2-one (120 mg, 0.397 mmol) in dichloromethane (2 mL) was added 1M boron tribromide in dichloromethane (400 μL, 0.400 mmol). The mixture was stirred at room temperature for 18 hours. The resultant mixture was poured into a saturated aqueous sodium bicarbonate solution. The precipitated solid was collected by filtration, purified by silica gel column chromatography (chloroform/methanol=97/3), and recrystallized from DMF/methanol to give the titled compound as a yellow crystal (41 mg, yield 36%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. custompurified by silica gel column chromatography (chloroform/methanol=97/3)
  3. customrecrystallized from DMF/methanol

Sources & evidence

ORD record
ord-079883211f58479f92f48dd438e43fa1
Source dataset
uspto-grants-2014_03
Patent number
US08680110B2

Reaction notes

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