Benzyl Bromide → HCID 53922389, compound

HRID 363298Notes

Reaction equation

HRID 363298 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][S:9](=[O:12])(=[O:11])[CH2:8][O:7][C:6]=2[CH:13]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.C(OCC)(=O)C>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:9](=[O:12])(=[O:11])[CH2:8][O:7][C:6]=2[CH:13]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22728543Water ethylacetateHCID 53745759HCID 53745759, compound

Product 1

HCID 53922389HCID 53922389, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of the title compound of Step D (0.5 g, 2.46 mmol), K2CO3 (1.02 g, 7.38 mmol), benzyl bromide (0.463 g, 2.71 mmol) and TBAB (79 mg) in DMF (5 mL) was stirred at room temperature for 48 h. After the reaction was complete, the reaction mixture was poured into an H2O/ethyl acetate mixture (10/100 mL). The organic phase was separated, dried and concentrated to give the title compound of Step E as a brown solid (0.76 g). 1H NMR (CDCl3, 300 MHz): δ 7.32 (m,6H, aromatic) 6.72 (d,1H, 11 Hz), 6.34 (d,1H, 8 Hz), 4.82 (s,2H), 4.69 (s,2H).

Workup

  1. customThe organic phase was separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-62bc8b92bd3240c8823d46bcd7e5f226
Source dataset
uspto-grants-1999_02
Patent number
US05874382

Reaction notes

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