Boron tribromide → HCID 18174429, compound

HRID 427611Notes

Reaction equation

HRID 427611 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-70bd7261801248609d7c5422e3a961bc
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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