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

HRID 594068

反応式

HRID 594068 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 116163143-bromo-4-(bromomethyl)benzoic Acid収率 60%

試薬・触媒・溶媒 1

HCID 7368(Trifluoromethyl)benzene溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a5833216af294f4aa238714c4ebbf9dd
出典データセット
uspto-grants-2016_01
特許番号
US09242969B2

関連ノート

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