Hydrogen Peroxide → 5-Bromo-3-methylthiophene-2-carboxylic acid

HRID 1465919노트

반응식

HRID 1465919 반응식
P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[OH:9]O.[Br:11][C:12]1[S:16][C:15]([CH:17]=[O:18])=[C:14]([CH3:19])[CH:13]=1.[Na]>O.C(#N)C>[Br:11][C:12]1[S:16][C:15]([C:17]([OH:9])=[O:18])=[C:14]([CH3:19])[CH:13]=1

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 24243Trisodium PhosphateHCID 5360545SodiumHCID 151154075-Bromo-3-methylthiophene-2-carbaldehyde

생성물 1

HCID 181766635-Bromo-3-methylthiophene-2-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

A solution of 50.4 g of sodium phosphate, monobasic, (1.5 mol) in 600 mL of water, followed by 131 mL of a 35% hydrogen peroxide solution were added to a solution of 5-bromo-3-methyl-thiophene-2-carbaldehyde (300 g, 1.46 mol), example 1-a, in 1.5 L of acetonitrile. The resultant solution was cooled to 0° C. with an external ice bath, and a solution of 170 g of sodium perchlorite in 2 L of water was added dropwise over a 2 hour period. The reaction mixture was allowed to warm to room temperature, and stirred for 1.5 h. The reaction was quenched with the addition of 10 g of sodium sulfite, and stirred for 15 min. The mixture was acidified to ca. pH 3 with 1 N HCl solution, and cooled to 0° C. An off-white precipitate was collected on a medium glass filter funnel. The precipitate was washed twice with water and then dissolved in ethyl acetate. The aqueous acetonitrile solution was extracted once with ethyl acetate, and the organic fraction was combined with the pervious ethyl acetate solution. The combined organic fractions were dried over anhydrous magnesium sulfate and concentrated under hi-vacuum to produce 305 g of a tan solid. 1H NMR (CDCl3, 200 MHz): δ=6.91 (s, 1H), 2.52 (s, 3H); MS: (−) m/z 218.92, 220.94 (M−1, 79Br/81Br)

후처리

  1. customThe reaction was quenched with the addition of 10 g of sodium sulfite
  2. stirringstirred for 15 min
  3. temperaturecooled to 0° C
  4. customAn off-white precipitate was collected on a medium glass
  5. filtrationfilter funnel
  6. washThe precipitate was washed twice with water
  7. dissolutiondissolved in ethyl acetate
  8. extractionThe aqueous acetonitrile solution was extracted once with ethyl acetate
  9. dry with materialThe combined organic fractions were dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under hi-vacuum

출처 및 근거

ORD 기록
ord-895aaa10bb5e48398286418ae44d2597
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000006B2

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