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

HRID 1012108노트

반응식

HRID 1012108 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 190422703-(Bromomethyl)-2-fluorobenzoic acid수율 17.5%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-544a0d8953064465ad30eb1a7caabb66
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977477B2

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