Dimethylamine → Methyl 3-bromo-5-((dimethylamino)methyl)benzoate

HRID 1845330ノート

反応式

HRID 1845330 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]=O)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:14][NH:15][CH3:16].C1COCC1.C([BH3-])#N.[Na+]>O.[Cl-].[Cl-].[Zn+2].CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:15]([CH3:16])[CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

8

反応物 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 11436457Methyl 3-bromo-5-formylbenzoate

生成物 1

HCID 58187962Methyl 3-bromo-5-((dimethylamino)methyl)benzoate

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A mixture of methyl 3-bromo-5-formylbenzoate (200 mg, 0.82 mmol), methanol (3 mL), 2.0 M dimethylamine solution in THF (0.3 mL, 6 mmol), zinc dichloride (30 mg, 0.22 mmol), and sodium cyanoborohydride (200 mg, 3.2 mmol) was stirred at 0° C. for 1 h. The mixture was diluted with water (10 mL) and the aqueous layer was extracted with EtOAc (15 mL×3). The combined organic layers were dried over anhydrous MgSO4 and concentrated. The residue was purified by silica gel chromatography to afford the title compound.

後処理

  1. extractionthe aqueous layer was extracted with EtOAc (15 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-4a97d3ccf2bb4cebb2125f3d7ef959f8
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

読み込み中…