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

HRID 1426304ノート

反応式

HRID 1426304 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].BrC1C=C(C(OC)=O)C=C(C=1)C(OC)=O.[CH3:29][NH:30][CH3:31].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:30]([CH3:31])[CH3:29])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

8

反応物 6

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11436457Methyl 3-bromo-5-formylbenzoate

生成物 1

HCID 58187962Methyl 3-bromo-5-((dimethylamino)methyl)benzoate収率 93%

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 WO2003/048111 starting from dimethyl 5-bromoisophthalate (Alfa Aesar) in methylene chloride (20 mL) was added a solution of 2.0M dimethylamine in tetrahydrofuran (7.4 mL, 15 mmol) and the reaction was stirred for 15 min. Sodium triacetoxyborohydride (4.7 g, 22 mmol) was then added and the resulting mixture was stirred overnight. Saturated sodium bicarbonate solution was added and the resulting mixture was extracted with ethyl acetate. The organic extract was washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated to afford product as a light yellow oil (1.87 g, 93%). 1H NMR (400 MHz, CDCl3) δ 8.08-8.03 (m, 1H), 7.90-7.87 (m, 1H), 7.70-7.67 (m, 1H), 3.91 (s, 3H), 3.42 (s, 2H), 2.24 (s, 6H); LCMS (M+H)+: 272.0, 274.0.

後処理

  1. stirringthe resulting mixture was stirred overnight
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed twice with water, once with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b4c2871d2fe64dfab8422307547299cc
出典データセット
uspto-grants-2015_01
特許番号
US08933085B2

反応ノート

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