3-(2-Bromo-5-(trifluoromethyl)phenyl)propanoic acid → 5-(Trifluoromethyl)indan-1-one

HRID 2244906ノート

反応式

HRID 2244906 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][CH2:13][C:14]([OH:16])=O.C([Li])CCC>C1COCC1.CCCCCC>[F:11][C:8]([F:9])([F:10])[C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[C:14](=[O:16])[CH2:13][CH2:12]2

参加物

5

反応物 2

HCID 248204723-(2-Bromo-5-(trifluoromethyl)phenyl)propanoic acidHCID 178418339Butyllithium

生成物 1

HCID 121749875-(Trifluoromethyl)indan-1-one収率 37.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒2 回

実験手順

To a solution of 3-[2-bromo-5-(trifluoromethyl)phenyl]propanoic acid (2.8 g, 9.4 mmol) in THF (100 mL) and hexane (20 mL) at −78° C. was dropwise added a 2.5 M solution of n-butyllithium in hexane (8.3 mL). After the addition had been completed, the reaction was quenched with saturated NH4Cl. The resulting solution was extracted with ethyl acetate twice. The extracts were washed with saturated NaHCO3, brine, dried over MgSO4 and concentrated. The crude material was purified by flash chromatography on silica eluting with 10-20% EtOAc/hexane to afford the desired product as a white solid (0.7 g, 37%). LC/MS calculated for C10H7F3O: (M+H)+ 201; found 201.1.

後処理

  1. additionAfter the addition
  2. customthe reaction was quenched with saturated NH4Cl
  3. extractionThe resulting solution was extracted with ethyl acetate twice
  4. washThe extracts were washed with saturated NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica eluting with 10-20% EtOAc/hexane

出典と根拠

ORDレコード
ord-44079c409f4d44e2937243c975bca67c
出典データセット
uspto-grants-2010_03
特許番号
US07678798B2

反応ノート

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