Boron trifluoride etherate → 2-(5-Bromo-2-methoxybenzyl)-1-benzothiophene

HRID 604708Notes

Reaction equation

HRID 604708 reaction equation
[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[CH:26]([C:28]1[CH:33]=[C:32]([Br:34])[CH:31]=[CH:30][C:29]=1[O:35][CH3:36])O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:34][C:32]1[CH:31]=[CH:30][C:29]([O:35][CH3:36])=[C:28]([CH:33]=1)[CH2:26][C:18]1[S:17][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 61406666(1-Benzothien-2-yl)(5-bromo-2-methoxyphenyl)methanol

Product 1

HCID 184504602-(5-Bromo-2-methoxybenzyl)-1-benzothiopheneYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Then, Et3SiH (10.3 mL, 0.0642 mol) and BF3.Et2O (4.10 mL, 0.0321 mol) were added sequentially to a chloroform (110 mL) solution of (1-benzothien-2-yl)(5-bromo-2-methoxyphenyl)methanol (1.2 g, 0.0321 mol) at −15° C. After the mixture was stirred for 0.5 hours, a saturated sodium bicarbonate aqueous solution was added. The mixture was extracted with chloroform, and the organic phase was washed with brine and then dried with anhydrous magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain a title compound (9.84 g, 92%) as a yellow crystal.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washthe organic phase was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe residue obtained
  5. customby evaporating the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-88f7099b8ce646b1b413e313e190da9e
Source dataset
uspto-grants-2011_03
Patent number
US07910619B2

Reaction notes

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