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

HRID 1845330노트

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HRID 1845330 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 887Methanol용매HCID 962Water용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4a97d3ccf2bb4cebb2125f3d7ef959f8
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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