Boron trifluoride etherate → 1-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzene

HRID 576334Notes

Reaction equation

HRID 576334 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:19][CH3:20])[C:5]([Cl:18])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:8][C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([O:19][CH3:20])[C:5]=2[Cl:18])=[CH:11][CH:12]=1)[CH3:17]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 71110682(5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanone

Product 1

HCID 710770511-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzeneYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 61 (4.45 g, 12.6 mmol) in CH2Cl2 (80 mL) was added dropwise triethylsilane (6.00 mL, 37.8 mmol) and boron trifluoride diethyl etherate (4.67 mL, 37.8 mmol) at 0° C. under an atmosphere of nitrogen. After being stirred for 5 hours at room temperature, the mixture was quenched with aq. saturated K2CO3 solution (30 mL) and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 62 (2.40 g, 56%) as colorless oil.

Workup

  1. customthe mixture was quenched with aq. saturated K2CO3 solution (30 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-30339ba797054e6bba0d5dcbfcb86040
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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