Boron trifluoride etherate → 1-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methoxybenzene

HRID 604741Notes

Reaction equation

HRID 604741 reaction equation
[SiH](CC)(CC)CC.B(F)(F)F.C[CH2:13][O:14]CC.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:37])=[C:22]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=2)=O)[C:23]=1OC.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.C(#N)C>[Br:17][C:18]1[C:19]([O:14][CH3:13])=[CH:20][C:21]([Cl:37])=[C:22]([CH2:26][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH3:36])=[CH:32][CH:33]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 67069096(5-Bromo-2-chloro-6-methoxyphenyl)(4-ethoxyphenyl)methanone

Product 1

HCID 670691051-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methoxybenzeneYield 102.5%

Reagents, catalysts & solvents 1

HCID 22555007Acetonitrile chloroformSolvent

Procedure

Then, Et3SiH (1.62 mL, 10.1 mmol) and BF3.Et2O (0.772 mL, 6.09 mmol) were added sequentially to a chloroform-acetonitrile (1:1; 16 mL) solution of (5-bromo-2-chloro-6-methoxyphenyl)(4-ethoxyphenyl)methanone (1.50 g, 4.06 mmol) at −5° C. The reaction mixture was warmed to room temperature and stirred for 16 hours. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain a colorless oily title compound (1.48 g, 99%).

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained
  6. customby evaporating the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b52cbb492d474c209d8263430bfad604
Source dataset
uspto-grants-2011_03
Patent number
US07910619B2

Reaction notes

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