Boron tribromide → 4-(4-chlorobenzyl)-6-bromo-2-(2-hydroxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1624903ノート

反応式

HRID 1624903 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([Br:14])=[N:10][N:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21]C)[C:8]2=[O:23])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([Br:14])=[N:10][N:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[OH:21])[C:8]2=[O:23])=[CH:24][CH:25]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 687023304-(4-chlorobenzyl)-6-bromo-2-(2-methoxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione

生成物 1

HCID 686988294-(4-chlorobenzyl)-6-bromo-2-(2-hydroxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione収率 91.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

According to Scheme 9 Step 1: To a solution of 4-(4-chlorobenzyl)-6-bromo-2-(2-methoxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione (150 mg, 0.35 mmol) in DCM (2 ml) cooled at −78° C. was added dropwise BBr3 (0.710 mL, 0.710 mmol). The reaction mixture was stirred 1 h at −78° C. and was quenched with MeOH. The mixture was allowed to reach room temperature. Water was added and the aqueous layer was extracted with DCM (×3). The combined organic layers were successively washed with water, brine, dried over MgSO4, filtered and concentrated. 131 mg (yield=90%) of 4-(4-chlorobenzyl)-6-bromo-2-(2-hydroxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione were recovered as a beige solid which was used in the next step without any purification.

後処理

  1. customwas quenched with MeOH
  2. customto reach room temperature
  3. additionWater was added
  4. extractionthe aqueous layer was extracted with DCM (×3)
  5. washThe combined organic layers were successively washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-90f92e531b004a37993d887e756cb70d
出典データセット
uspto-grants-2014_07
特許番号
US08779129B2

反応ノート

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