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

HRID 1617398노트

반응식

HRID 1617398 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].O1CCCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[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

7

반응물 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11436457Methyl 3-bromo-5-formylbenzoate

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 3-bromo-5-formylbenzoate (1.8 g, 7.4 mmol, prepared as described in WO 2003048111 from dimethyl 5-bromoisophthalate, Alfa Aesar) in methylene chloride (20 mL) was added a solution of 2.0 M dimethylamine in tetrahydrofuran (7.4 mL, 15 mmol). This mixture was stirred for 15 minutes, followed by the addition of sodium triacetoxyborohydride (4.7 g, 22 mmol). The resulting mixture was stirred overnight. Saturated sodium bicarbonate solution was added and the product was extracted with ethyl acetate. The combined organic extracts were washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated to afford a light yellow oil. Yield: 1.87 g (93%); LC-MS: 272.0, 274.0 (M+H)+. 1H NMR (400 MHz, CDCl3): δ 8.06 (dd, 1H), 7.89 (dd, 1H), 7.69 (dd, 1H), 3.91 (s, 3H), 3.42 (s, 2H), 2.24 (s, 6H).

후처리

  1. stirringThe resulting mixture was stirred overnight
  2. extractionthe product was extracted with ethyl acetate
  3. washThe combined organic extracts were washed twice with water, once with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a light yellow oil

출처 및 근거

ORD 기록
ord-88b9442b4ca740a882603af2b2a1384b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765734B2

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