Diethyl Ether → N-Benzyl-3-hydroxy-5-iodo-benzamide

HRID 1670070ノート

反応式

HRID 1670070 の反応式
[CH2:1]([NH:8][C:9](=[O:19])[C:10]1[CH:15]=[C:14]([O:16]C)[CH:13]=[C:12]([I:18])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(OCC)C>ClCCl.C(=O)=O.CC(C)=O>[CH2:1]([NH:8][C:9](=[O:19])[C:10]1[CH:11]=[C:12]([I:18])[CH:13]=[C:14]([OH:16])[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 57905830N-benzyl-3-iodo-5-methoxy-benzamide

生成物 1

HCID 57905909N-Benzyl-3-hydroxy-5-iodo-benzamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 18522661Acetone cardice溶媒

実験手順

A solution of N-benzyl-3-iodo-5-methoxy-benzamide (4.7 g) in anhydrous dichloromethane (100 mL) was cooled to −78° C. in dry ice/acetone bath under flow of argon and a BBr3 solution (38.4 mL of 1 M solution in dichloromethane) was added dropwise. After the addition was completed, the reaction mixture was stirred at room temperature overnight. The reaction mixture was cooled in an ice bath and then quenched by a dropwise addition of methanol. Then it was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and concentrated to remove the solvents. The title compound was obtained by trituration with diethyl ether and hexanes (4.1 g, 90% yield).

後処理

  1. additionAfter the addition
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customquenched by a dropwise addition of methanol
  4. additionThen it was diluted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto remove the solvents

出典と根拠

ORDレコード
ord-3374d53e150c4a28b06d3cf01f46ad1e
出典データセット
uspto-grants-2011_08
特許番号
US07989454B2

反応ノート

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