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 585128노트

반응식

HRID 585128 반응식
[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]

참가 물질

4

반응물 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

생성물 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 acid수율 52.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cb34fa63b00e4be18640a401a1fd3678
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930107B2

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