Iodine → 4-Chloro-2-fluoro-6-iodobenzoic acid

HRID 596054

反応式

HRID 596054 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.C(O)(=O)C.C(O)(=O)C.[I:20]C1C=CC=CC=1.II.CN(C=O)C>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:10]=[C:9]([I:20])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1

参加物

7

反応物 4

HCID 807IodineHCID 6228DimethylformamideHCID 991524-Chloro-2-fluorobenzoic acid2 回HCID 12217721Iodo benzene diacetate

生成物 1

HCID 1180459354-Chloro-2-fluoro-6-iodobenzoic acid

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a 250 mL flask were added 4-chloro-2-fluorobenzoic acid (4 g, 22.92 mmol), Pd(OAc)2 (0.257 g, 1.146 mmol), iodobenzene diacetate (8.12 g, 25.2 mmol), iodine (6.40 g, 25.2 mmol) and DMF (60 mL). The solution was heated under a nitrogen atmosphere at 100° C. for 20 h. LCMS showed about half of 4-chloro-2-fluorobenzoic acid was converted to the product (LCMS retention time 0.98 min, no MH+ peak). After cooling to room temperature, the solution was diluted with EtOAc and washed three times with 1 N HCl. The aqueous layers were combined and extracted once with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to give a dark brown oil (16.4 g, 42% pure), which was taken to the next step without purification.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed three times with 1 N HCl
  3. extractionextracted once with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a dark brown oil (16.4 g, 42% pure), which
  7. customwas taken to the next step without purification

出典と根拠

ORDレコード
ord-3f19965fe351414d9c0e744a7d758022
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

関連ノート

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