Sodium Bicarbonate → HCID 13225968, 화합물

HRID 1640329노트

반응식

HRID 1640329 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 13225968HCID 13225968, 화합물

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4ea146ff678d4503b81dfc10b9d235df
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114382B2

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