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

HRID 490219ノート

反応式

HRID 490219 の反応式
[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]

参加物

8

反応物 4

HCID 260Hydrogen Bromide2 回HCID 947NitrogenHCID 27744002-Amino-3-bromo-5-methylbenzoic acidHCID 23668193Sodium Nitrite

生成物 1

HCID 218526502,3-Dibromo-5-methylbenzoic acid

試薬・触媒・溶媒 3

HCID 24593copper(I) bromide触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-7fcdbe3b791a49d199096055ef257fa4
出典データセット
uspto-grants-2009_05
特許番号
US07528134B2

反応ノート

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