Chlorosuccinimide → 2-Chloro-5-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

HRID 521457ノート

反応式

HRID 521457 の反応式
OC1C=C(C=CC=1OC)C(OC)=O.[Cl:14]C1C=C(CCO)C=CC=1.[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[CH:28]=1.ClN1C(=O)CCC1=O>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:28]=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[C:30]([O:33][CH3:34])=[CH:31][C:32]=1[Cl:14]

参加物

7

反応物 4

HCID 31398ChlorosuccinimideHCID 78856m-Chlorophenethylic alcoholHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 670762963-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

生成物 1

HCID 670763362-Chloro-5-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-触媒HCID 6344Dichloromethane溶媒

実験手順

Methyl 3-hydroxy-4-methoxybenzoate and 2-(3-chlorophenyl)-ethanol were reacted in analogy to step 1 of example 1. The obtained 3-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester (300 mg, 0.935 mmol), N-chloro-succinimide (381 mg, 2.81 mmol), and zirconium tetrachloride (129 mg, 0.57 mmol) were suspended in DCM (4 ml) and the mixture was stirred under reflux for 5 h until the starting material was used up. The mixture was partitioned between EA and a saturated aqueous sodium hydrogencarbonate solution, the aqueous phase extracted with EA, and the combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica chromatography (HEP/EA gradient) to give 118 mg of the title compound.

後処理

  1. temperatureunder reflux for 5 h until the starting material
  2. customThe mixture was partitioned between EA
  3. extractiona saturated aqueous sodium hydrogencarbonate solution, the aqueous phase extracted with EA
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by silica chromatography (HEP/EA gradient)

出典と根拠

ORDレコード
ord-af669e1dd417421e9f1cfc1046f29a7f
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

反応ノート

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