2,6-Lutidine → 5-Hydroxy-2-methyl-benzofuran-7-carboxylic acid methyl ester

HRID 1177071

反応式

HRID 1177071 の反応式
B(Br)(Br)Br.[CH3:5][O:6][C:7]([C:9]1[C:17]2[O:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH:12]=[C:11]([O:19]C)[CH:10]=1)=[O:8].N1C(C)=CC=CC=1C>C(Cl)Cl>[CH3:5][O:6][C:7]([C:9]1[C:17]2[O:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH:12]=[C:11]([OH:19])[CH:10]=1)=[O:8]

参加物

5

反応物 3

HCID 79372,6-LutidineHCID 25134Boron tribromideHCID 595604655-Methoxy-2-methyl-benzofuran-7-carboxylic acid methyl ester

生成物 1

HCID 595603415-Hydroxy-2-methyl-benzofuran-7-carboxylic acid methyl ester収率 83.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

BBr3 (10 mL, 10.08 mmol, 1.0 M in CH2Cl2) was added drop-wise to a solution of 5-methoxy-2-methyl-benzofuran-7-carboxylic acid methyl ester (4c) (951 mg, 4.31 mmol) and 2,6-lutidine (1.17 mL, 10.08 mmol) in CH2Cl2 (20 mL) at 0° C. The mixture was stirred and warmed to RT overnight. The mixture was quenched with H2O (60 mL) and extracted with CH2Cl2 (2×60 mL). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 5% CH3OH/CH2Cl2 to afford a white solid (746 mg, 83%). 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J=2.53 Hz, 1 H) 7.13 (d, J=2.53 Hz, 1 H) 6.33 (d, J=1.01 Hz, 1 H) 5.50 (s, 1 H) 4.00 (s, 3 H) 2.49 (d, J=1.01 Hz, 3 H).

後処理

  1. customThe mixture was quenched with H2O (60 mL)
  2. extractionextracted with CH2Cl2 (2×60 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatograph
  6. washeluting with 5% CH3OH/CH2Cl2

出典と根拠

ORDレコード
ord-420395d26df34f17a33ef92591f3ee43
出典データセット
uspto-grants-2010_11
特許番号
US07842713B2

関連ノート

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