Benzyl Bromide → HCID 53922389, compound

HRID 1289368Notes

Reaction equation

HRID 1289368 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.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.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]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:9](=[O:12])(=[O:11])[CH2:8][O:7][C:6]=2[CH:13]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 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), K2 CO3 (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 H2 O/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): δ7.32 (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-370d93818f034f8eadd573a119d369e1
Source dataset
uspto-grants-1998_05
Patent number
US05750471

Reaction notes

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