N-bromobutanimide → HCID 18002687, compound

HRID 478698Notes

Reaction equation

HRID 478698 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:23]N1C(=O)CCC1=O>ClCCl>[Br:23][C:12]1[CH:11]=[CH:10][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:22])[F:21])=[N:17]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18002704HCID 18002704, compound

Product 1

HCID 18002687HCID 18002687, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 8-(tert-butyldimethylsilanyloxy)-2-trifluoromethylquinoline (17.5 g) in dichloromethane (100 ml) was treated with N-bromosuccinimide (10.5 g) at 15° C. The mixture was stirred at 20° C. for 25 minutes, washed with 1% sodium sulfite solution (100 ml), and water (50 ml). The organic layer was separated, dried over magnesium sulfate, filtered and the solvent removed in vacuo to give the product (21.4 g) as a dark oil.

Workup

  1. washwashed with 1% sodium sulfite solution (100 ml), and water (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b0e4b73e5a5548ecb6862b2720b23508
Source dataset
uspto-grants-2003_11
Patent number
US06642254B2

Reaction notes

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