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 585128ノート

反応式

HRID 585128 の反応式
[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]

参加物

4

反応物 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

生成物 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 acid収率 52.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cb34fa63b00e4be18640a401a1fd3678
出典データセット
uspto-grants-2005_08
特許番号
US06930107B2

反応ノート

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