Boron tribromide → HCID 18174429, compound

HRID 395759Notes

Reaction equation

HRID 395759 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:32])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:32])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:31])[C:21]2[CH:22]=[CH:23][C:24]([C:27]([CH3:28])([CH3:29])[CH3:30])=[CH:25][CH:26]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 18174579HCID 18174579, compound

Product 1

HCID 18174429HCID 18174429, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension N-(3,5-dimethoxyphenyl)-2-[(4-tert-butylbenzoyl)amino]benzamide (1.0 g, 2.3 mmol) in dichloromethane (42 mL) was added a solution of boron tribromide (0.66 mL, 6.9 mmol) in dichloromethane (7 mL) via an addition funnel. After 30 min, a second portion of boron tribromide (0.66 mL, 6.9 mmol) in dichloromethane (7 mL) was added. After 30 min, saturated aqueous sodium bicarbonate solution was added and the solvents were removed in vacuo. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 30% ethyl acetate/70% hexanes) provided 96 mg (10%) of the title compound as a white solid.

Workup

  1. waitAfter 30 min
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8a86687519248fab7529cde4d5c018e
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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