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

HRID 72609Notes

Reaction equation

HRID 72609 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1807c45f54754e01adefbce5d50c9cab
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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