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

HRID 1258851ノート

反応式

HRID 1258851 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7a63765dbb004218a5584f8dc1e0caf8
出典データセット
uspto-grants-2013_06
特許番号
US08466114B2

反応ノート

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