Hydrogen Bromide → 3-Bromo-4-(trifluoromethyl)benzoic acid

HRID 586019

반응식

HRID 586019 반응식
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].NC(N)=O.[OH-].[Na+].[BrH:25]>O>[Br:25][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6]

참가 물질

7

반응물 5

HCID 260Hydrogen Bromide2회HCID 1176UreaHCID 14798Sodium HydroxideHCID 6426513-Amino-4-(trifluoromethyl)benzoic acidHCID 23668193Sodium Nitrite

생성물 1

HCID 223375703-Bromo-4-(trifluoromethyl)benzoic acid

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
75 °C

실험 절차

3-Amino-4-trifluoromethylbenzoic acid (8.20 g, 40.0 mmol), prepared according to Astrid Giencke and Helmut Lackner, Liebigs Ann. Chem., 569-579:6 (1990), in 48% HBr (20 mL) and H2O (67 mL) at 0° C. was treated with NaNO2 (2.99 g) in small portions over 15 minutes. After stirring for 30 minutes, the mixture was treated with urea (0.250 g) and then the mixture was added dropwise to a solution of CuBr (10.0 g) in 48% HBr (40 mL) and H2O (100 mL). The reaction mixture was heated at 75° C., stirred for 2 hours, cooled to room temperature, and stirred overnight. The mixture was treated with with 20% NaOH until the pH>10. The resulting blue copper salts were removed by filtration through Celite. The mixture was acidified to pH 1 with HCl, extracted with CH2Cl2 (3×200 mL), dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to provide the title compound.

후처리

  1. stirringstirred for 2 hours
  2. temperaturecooled to room temperature
  3. stirringstirred overnight
  4. customThe resulting blue copper salts were removed by filtration through Celite
  5. extractionextracted with CH2Cl2 (3×200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-009882c007344d3aab7baa74d8e1f325
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933311B2

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