Sodium Bromide → Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate

HRID 2177716ノート

反応式

HRID 2177716 の反応式
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([OH:22])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.O.[F-].[K+].[Br-].[Na+]>FC(F)(F)C1C=CC=CC=1.O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([OH:22])[C:14]([C:26]3[CH:27]=[CH:28][O:24][CH:25]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 253881Sodium BromideHCID 2734358Furan-3-boronic acidHCID 23675105Potassium fluoride hydrateHCID 67108192Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate2 回

生成物 1

HCID 67107629Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate収率 66.2%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 7368(Trifluoromethyl)benzene溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
175 °C

実験手順

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate (Intermediate 52, 0.39 g), furan-3-yl boronic acid (0.16 g), potassium fluoride monohydrate (0.45 g), tetrakis-(triphenylphosphine) palladium (0.11 g), and sodium bromide (0.15 g) in α,α,α-trifluorotoluene (10 ml) and dioxane (2 ml) was degassed and heated in the microwave at 175° C. for 30 minutes. After cooling, the mixture was partitioned between ethyl acetate and water. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-30% to give ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate (0.25 g) as a white solid.

後処理

  1. customwas degassed
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-30%

出典と根拠

ORDレコード
ord-4a45f12542fd4752b1991aaef5358c6a
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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