Azobisisobutyronitrile → 3-(Bromomethyl)-2-fluorobenzoic acid

HRID 1012108ノート

反応式

HRID 1012108 の反応式
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:10]1[C:2]([F:1])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27373792-Fluoro-3-methylbenzoic acid

生成物 1

HCID 190422703-(Bromomethyl)-2-fluorobenzoic acid収率 17.5%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 2-fluoro-3-methylbenzoic acid (0.462 g, 3 mmol), N-bromosuccinimide (0.560 g, 3.15 mmol), azobisisobutyronitrile (AIBN) (0.024 g, 0.15 mmol) and CCl4 (10 ml) was heated at reflux for 18 h. The reaction mixture was then reduced in vacuo and partitioned between ethyl acetate and aqueous K2CO3. The aqueous layer was acidified (2M HCl) and cooled in ice. The precipitate obtained was collected by filtration and dried in vacuo to give 3-bromomethyl-2-fluoro-benzoic acid (0.1225 g, 13%) as a colourless solid. (LC/MS: Rt 3.18, [M−H]− 232.91).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. custompartitioned between ethyl acetate and aqueous K2CO3
  4. temperaturecooled in ice
  5. customThe precipitate obtained
  6. filtrationwas collected by filtration
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-544a0d8953064465ad30eb1a7caabb66
出典データセット
uspto-grants-2011_07
特許番号
US07977477B2

反応ノート

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