Triethylsilane → 6-(2-Bromo-5-iodo-benzyl)-chroman

HRID 72603Notes

Reaction equation

HRID 72603 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:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH2:16][CH2:15][CH2:14]2)=O.C([SiH](CC)CC)C>C(#N)C.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH2:9][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH2:16][CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 58340801(2-Bromo-5-iodo-phenyl)-chroman-6-yl-methanone

Product 1

HCID 583408156-(2-Bromo-5-iodo-benzyl)-chromanYield 77.5%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a stirred solution of (2-bromo-5-iodo-phenyl)-chroman-6-yl-methanone (2.0 g, 4.51 mmol) in acetonitrile: dichloromethane (2:1 mixture, 9 mL) was added triethylsilane (2.52 mL, 15.78 mmol) and boron trifluoride diethyl etherate complex 1.11 mL, 9.02 mmol) at 0° C. After stirring overnight at room temperature, reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution. Volatiles were evaporated under reduced pressure. The aqueous layer was extracted with ethyl acetate (2×20 mL). Ethyl acetate layer was washed with water, brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 6-(2-bromo-5-iodo-benzyl)-chroman (1.5 g).

Workup

  1. customreaction
  2. customwas quenched by the addition of saturated aqueous sodium bicarbonate solution
  3. customVolatiles were evaporated under reduced pressure
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  5. washEthyl acetate layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-be4dfb06f0b54a298f04052f5f31f3af
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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