Boron tribromide → Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate

HRID 2177725ノート

反応式

HRID 2177725 の反応式
B(Br)(Br)Br.[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([O:26]C)[C:18]([Br:28])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([OH:26])[C:18]([Br:28])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2 回

生成物 1

HCID 67108192Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate収率 73.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Boron tribromide (1M solution in DCM, 5.85 ml) was added dropwise to a stirred, cooled solution of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 2.3 g) in dry DCM (45 ml) at −70° C. The resultant mixture was stirred at −70° C. for 40 minutes, then allowed to warm to room temperature. It was stirred at room temperature for 2 hours then poured into sodium bicarbonate (saturated aqueous solution). The layers were separated and the aqueous layer was extracted with further DCM. The combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate (1.64 g) as a white solid.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with further DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-9b388b3b5dff40f0b2e05f1f08aa39c7
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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