Boron tribromide → dimethyl 2-hydroxyisophthalate

HRID 2071146ノート

反応式

HRID 2071146 の反応式
B(Br)(Br)Br.C[O:6][C:7]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]>C(Cl)Cl>[OH:6][C:7]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 15708503Dimethyl 2-methoxybenzene-1,3-dicarboxylate

生成物 1

HCID 10889156dimethyl 2-hydroxyisophthalate収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

BBr3 (1.0M in CH2Cl2, 7.53 ml, 7.53 mmol, 2.5 eq) was added dropwise to a stirred solution of dimethyl 2-methoxyisophthalate (0.6785 g, 3.01 mmol, 1 eq) in anhydrous CH2Cl2 (4 ml) at 0° C. under Ar. After 30 min the reaction was warmed to room temperature. After 2 h the reaction was quenched anhydrous MeOH (1 ml) and stirred overnight. The solvent was removed in vacuo and the residue dissolved in EtOAc. The organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.4045 g (1.92 mmol, 64% yield) of dimethyl 2-hydroxyisophthalate.

後処理

  1. customAfter 2 h the reaction was quenched anhydrous MeOH (1 ml)
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1)
  5. dry with materialdried over Na2SO4
  6. filtrationThe inorganics were filtered off
  7. customthe solvent was removed in vacuo
  8. customPurification via flash chromatography

出典と根拠

ORDレコード
ord-7cf5219e43044c9caa4730a57144713f
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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