Sodium Bicarbonate → HCID 13225968、化合物

HRID 1640329ノート

反応式

HRID 1640329 の反応式
[Br:1][C:2]1[O:3][C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[C:6]=1[CH2:7]Br.C([O-])(O)=[O:14].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[O:3][C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[C:6]=1[CH2:7][OH:14]

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 123374992-Bromo-3-(bromomethyl)-1-benzofuran

生成物 1

HCID 13225968HCID 13225968、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

2-bromo-3-bromomethyl benzofuran prepared from Step A (7.67 g, 26.45 mmol) was immediately dissolved in dioxane (30 mL), followed by a solution of NaHCO3 (2.67 g, 1.2 eq.) in water (30 mL). The mixture was refluxed for 1 h with vigorous stirring, cooled to room temperature, diluted with water (150 mL) and extracted with dichloromethane (5×100 mL). The extract was washed with brine, dried over sodium sulfate, and the solvent removed under reduced pressure. The resulting orange oil was dissolved in chloroform (12 mL) and left to stand at −20° C. The resulting yellow prisms were filtered at −40° C., washed with chloroform, and filtered cold. Yield: 3.72 g (62%). MS (m/e): 228, 226 (M+), 211, 209, 183, 181, 171, 169, 147, 118, 102, 91. 1H-NMR (acetone-D6): 4.29 (t, 1H, J=6 Hz) 4.73 (d, 2H, J=6 Hz) 7.32 (m, 2H) 7.51 (d, 1H, J=8 Hz) 7.78 (dd, 1H, J=8 Hz, 2 Hz). 13C-NMR (acetone-D6): 54.74, 110.64, 119.96, 123.28, 124.57, 126.51, 128.12, 155.37.

後処理

  1. temperatureThe mixture was refluxed for 1 h with vigorous stirring
  2. extractionextracted with dichloromethane (5×100 mL)
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe resulting orange oil was dissolved in chloroform (12 mL)
  7. waitleft
  8. customto stand at −20° C
  9. filtrationThe resulting yellow prisms were filtered at −40° C.
  10. washwashed with chloroform
  11. filtrationfiltered cold

出典と根拠

ORDレコード
ord-4ea146ff678d4503b81dfc10b9d235df
出典データセット
uspto-grants-2012_02
特許番号
US08114382B2

反応ノート

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