Boron tribromide → 2-[4-(3-Bromo-4-hydroxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid

HRID 585128Notes

Reaction equation

HRID 585128 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28]C)[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[C:15]([C:21]([OH:23])=[O:22])=[N:14]2)=[CH:8][C:7]=1[CH3:24].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[OH:28])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[C:15]([C:21]([OH:23])=[O:22])=[N:14]2)=[CH:8][C:7]=1[CH3:24]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 223394382-[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid

Product 1

HCID 223396682-[4-(3-Bromo-4-hydroxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acidYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (40 ml) of 2-[4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (800 mg) in methylene chloride (40 ml) was added boron tribromide (5.2 ml of a 1.0 M solution). After stirring for 18 h, the reaction mixture was poured over ice and stirred at room temperature for 3 h. The reaction was extracted three times with 1N potassium hydroxide, and the aqueous layers were combined, acidified to pH 2 with hydrochloric acid, and extracted three times with ethyl acetate. The organic phases were combined, washed with brine, dried and concentrated to give fluffy yellow solid (408 mg) of the title compound. MS Calc.447; Found: 446 (M−1).

Workup

  1. additionthe reaction mixture was poured over ice
  2. stirringstirred at room temperature for 3 h
  3. extractionThe reaction was extracted three times with 1N potassium hydroxide
  4. extractionextracted three times with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cb34fa63b00e4be18640a401a1fd3678
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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