Hydrogen Bromide → 2,3-Dibromo-5-methylbenzoic acid

HRID 490219노트

반응식

HRID 490219 반응식
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1N.N([O-])=O.[Na+].N#N.[BrH:19]>C(O)(=O)C.O.[Cu]Br>[Br:19][C:3]1[C:2]([Br:1])=[CH:10][C:9]([CH3:11])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

참가 물질

8

반응물 4

HCID 260Hydrogen Bromide2회HCID 947NitrogenHCID 27744002-Amino-3-bromo-5-methylbenzoic acidHCID 23668193Sodium Nitrite

생성물 1

HCID 218526502,3-Dibromo-5-methylbenzoic acid

시약·촉매·용매 3

HCID 24593copper(I) bromide촉매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a solution of 3-bromo-5-methylanthranilic acid (2.3 g, 10 mmol) in acetic acid (12 mL) at 0° C. was added 18% hydrobromic acid (30 mL, 30 mmol) followed by drop wise addition of a solution of sodium nitrite (690 mg, 10 mmol) in water (5 mL). After 10 min, this solution was added to a mixture of copper (I) bromide (2.15 g, 15 mmol) in 48% hydrobromic acid (7 mL) at 0° C. The mixture was allowed to warm to ambient temperature (15 minutes) and then refluxed at 50° C. until evolution of N2 was completed. The mixture was then extracted with ethyl acetate, washed with water, brine, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to provide 2.8 g of crude of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.27 (s, 3H), 7.43 (s, 1H), 7.72 (s, 1H), 13.60 (br s, 1H); MS (DCI/NH3) m/e 310 (M+NH4)+.

후처리

  1. extractionThe mixture was then extracted with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7fcdbe3b791a49d199096055ef257fa4
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528134B2

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