Triethylsilane → 4-Bromo-1-chloro-2-(4-methoxybenzyl)benzene

HRID 628749Notes

Reaction equation

HRID 628749 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.C(OC)(C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(#N)C.C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 12052TriethylsilaneHCID 15413tert-Butyl methyl etherHCID 516892Sodium BicarbonateHCID 22328608(5-Bromo-2-chloro-phenyl)-(4-ethoxy-phenyl)-methanone

Product 1

HCID 223285944-Bromo-1-chloro-2-(4-methoxybenzyl)benzeneYield 89.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

(5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone (265 g, 0.81 mol) was dissolved in methylene chloride (515 mL) and acetonitrile (1030 mL). To the resulting mixture was added triethyl silane (352 mL, 2.22 mol). Then to the resulting mixture was added dropwise boron trifluoride-diethyl etherate (273 mL, 2.22 mol) at 0° C. under a nitrogen protection. After the completion of dropwise addition, the resulting mixture was stirred for 20 min, warmed up to room temperature and reacted for 2 hr. TLC indicated the completion of reaction. To the reaction mixture were added methyl tert-butyl ether (1.5 L) and a saturated sodium bicarbonate solution (1.5 L). The mixture was stirred for 30 mins. The organic phase was separated off, washed with a saturated sodium bicarbonate solution for four times and with a saturated sodium chloride solution for one time, dried over anhydrous sodium sulphate, and evaporated by rotation to produce an oily substance. To the oily substance was added ethanol. The resulting mixture was stirred at room temperature for 30 mins and in an ice bath for 30 mins. A great quantity of solid was separated out and filtered. The filter cake was dried to produce 226 g of a product in a yield of 89%.

Workup

  1. additionAfter the completion of dropwise addition
  2. customreacted for 2 hr
  3. customthe completion of reaction
  4. stirringThe mixture was stirred for 30 mins
  5. customThe organic phase was separated off
  6. washwashed with a saturated sodium bicarbonate solution for four times and with a saturated sodium chloride solution for one time
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated by rotation
  9. customto produce an oily substance
  10. stirringThe resulting mixture was stirred at room temperature for 30 mins and in an ice bath for 30 mins
  11. customA great quantity of solid was separated out
  12. filtrationfiltered
  13. customThe filter cake was dried

Sources & evidence

ORD record
ord-42cd504f32144135aabaa497e3388d88
Source dataset
uspto-grants-2016_04
Patent number
US09315438B2

Reaction notes

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