Azobisisobutyronitrile → 3-bromo-4-(bromomethyl)benzoic Acid

HRID 594068

반응식

HRID 594068 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:31])C(=O)C1>FC(F)(F)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][Br:31])[C:5]([OH:7])=[O:6]

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 821303-Bromo-4-methylbenzoic acid

생성물 1

HCID 116163143-bromo-4-(bromomethyl)benzoic Acid수율 60%

시약·촉매·용매 1

HCID 7368(Trifluoromethyl)benzene용매

반응 조건

온도
90 °C

실험 절차

To a solution of 3-bromo-4-methylbenzoic acid (1.0 equiv.) and AIBN (0.05 equiv.) in trifluorotoluene (0.28 M) was added NBS (1.1 equiv.). The mixture was heated at 90° C. overnight. The reaction mixture was partitioned between EtOAc and H2O. The organic layer was washed with NaCl(sat.), dried over MgSO4, filtered, concentrated to yield 3-bromo-4-(bromomethyl)benzoic acid in 60% yield. LC/MS (m/z)=294.8 (MH+), Rt=0.80 min.

후처리

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. washThe organic layer was washed with NaCl(sat.)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a5833216af294f4aa238714c4ebbf9dd
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242969B2

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