Boron tribromide → HCID 90103002, compound

HRID 1052636Notes

Reaction equation

HRID 1052636 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)[C:5]([Cl:8])=[N:6][CH:7]=1.B(Br)(Br)Br>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 90102989HCID 90102989, compound

Product 1

HCID 90103002HCID 90103002, compoundYield 110.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(5-Bromo-2-chloropyridin-3-yl)-4-methoxybenzamide (1.4 g, 81% purity, 3.32 mmol) was dissolved in 80 mL dichloromethane. A solution of boron tribromide (1M in dichloromethane, 16.6 ml, 16.6 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and washed with a solution of 4% sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure to give 1.2 g (100% yield) of the title compound as an orange solid. Purity 91%.

Workup

  1. washwashed with a solution of 4% sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4c0c58c2385f4ac5ba4ce23737889960
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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