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

HRID 1617398ノート

反応式

HRID 1617398 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].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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-88b9442b4ca740a882603af2b2a1384b
出典データセット
uspto-grants-2014_07
特許番号
US08765734B2

反応ノート

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