Triethylsilane → 6-(2-Bromo-5-iodobenzyl)-2,3-dihydrobenzo[b][1,4]dioxine

HRID 72609노트

반응식

HRID 72609 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1)=O.C([SiH](CC)CC)C.OS(C(F)(F)F)(=O)=O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH2:9][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1

참가 물질

5

반응물 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 58340798Methanone, (2-bromo-5-iodophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)-

생성물 1

HCID 583408306-(2-Bromo-5-iodobenzyl)-2,3-dihydrobenzo[b][1,4]dioxine수율 91.2%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

To a stirred solution of (2-bromo-5-iodo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone (30.0 g, 67.4 mmol) in trifluoroacetic acid (100 mL) was added triethylsilane (86.2 mL, 539.3 mmol) followed by triflic acid (6.0 mL, 67.42 mmol) at room temperature. After stirring for 25 min at room temperature, volatiles were evaporated under reduced pressure. The resulting residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution (200 mL×2), water (200 mL), and brine (200 mL), then dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 6-(2-bromo-5-iodo-benzyl)-2,3-dihydro-benzo[1,4]dioxine (26.5 g).

후처리

  1. customvolatiles were evaporated under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate solution (200 mL×2), water (200 mL), and brine (200 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1807c45f54754e01adefbce5d50c9cab
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828951B2

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