Benzyl Bromide → HCID 23043964, compound

HRID 2165213Notes

Reaction equation

HRID 2165213 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:12]=2[CH2:21][C:22]#[N:23])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].C(Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl.CN(C)C=O>[C:3]1([CH2:1][O:2][C:3]2[CH:4]=[C:5]([CH2:9][CH2:10][C:11]3[C:16]([O:17][CH2:18][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[C:15]([O:19][CH2:20][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:14]=[CH:13][C:12]=3[CH2:21][C:22]#[N:23])[CH:6]=[CH:7][CH:8]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 23043867HCID 23043867, compound

Product 1

HCID 23043964HCID 23043964, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To the 2-[2-[(3-methoxyphenyl)ethyl]-3,4-dimethoxybenzeneacetonitrile (5 g) in dichloromethane (100 ml) at -78°, under nitrogen was added 1M boron tribromide (80 ml) in dichloromethane. The reaction was then stirred at room temperature for 4 hours. Ice/water (50 ml) was added and the aqueous extracted with ether. The ethereal layer was dried (MgSO4) and concentrated to give a purple oil. This oil was dissolved in dry dimethylformamide (100 ml) and then potassium carbonate (22.18 g) followed by benzyl bromide (16.5 g) were added. The reaction was stoppered and stirred at room temperature for 14 hours. Ice/water was added, the aqueous layer extracted with ether, the ethereal layer washed with brine, dried (MgSO4) and concentrated to give a yellow oil. This was purified by flash column chromatography on silica gel using ether:petroleum ether 40°-60°; 1:2; v/v to give 2.6 g of the sub-title compound as a white solid, mp 90° (softens) -95° -97° melts.

Workup

  1. extractionthe aqueous extracted with ether
  2. dry with materialThe ethereal layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customto give a purple oil
  5. additionwere added
  6. stirringstirred at room temperature for 14 hours
  7. extractionthe aqueous layer extracted with ether
  8. washthe ethereal layer washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a yellow oil
  12. customThis was purified by flash column chromatography on silica gel
  13. custompetroleum ether 40°-60°

Sources & evidence

ORD record
ord-7e0de0b1931e458dbb5b9116daba4cb0
Source dataset
uspto-grants-1990_07
Patent number
US04939147

Reaction notes

Loading…