Boron trifluoride etherate → 7-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methyl-2,3-dihydrobenzofuran

HRID 576354Notes

Reaction equation

HRID 576354 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]([CH3:11])[CH2:7][C:6]=2[C:5]([Cl:12])=[C:4]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)=O)[CH:3]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CC#N>[Br:1][C:2]1[C:10]2[O:9][CH:8]([CH3:11])[CH2:7][C:6]=2[C:5]([Cl:12])=[C:4]([CH2:13][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH3:23])=[CH:19][CH:20]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 71078368(7-Bromo-4-chloro-2-methyl-2,3-dihydrobenzofuran-5-yl)(4-ethoxyphenyl)methanone

Product 1

HCID 710769227-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methyl-2,3-dihydrobenzofuranYield 88.2%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of crude methanone 89 (3.15 g, 7.96 mmol) in CH2Cl2/CH3CN (25 mL/25 mL) were added triethylsilane (3.8 mL, 23.9 mmol) and boron trifluoride diethyl etherate (3.0 mL, 23.9 mmol) at 0° C. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 hours. To the mixture was added aq. saturated K2CO3 solution (70 mL) slowly and extracted with EtOAc (50 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by normal phase column chromatography to provide the desired product 90 (2.68 g, 85% (2-steps)).

Workup

  1. extractionextracted with EtOAc (50 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by normal phase column chromatography

Sources & evidence

ORD record
ord-855b92a10528405eae09f28404f6a669
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

Loading…