Bromine → HCID 12056719, compound

HRID 1060524Notes

Reaction equation

HRID 1060524 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1.[Br:19]Br>C(O)(=O)C>[Br:19][CH2:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 12056718HCID 12056718, compound

Product 1

HCID 12056719HCID 12056719, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

The title compound of Step B (2.0 g, 8 mmol) was dissolved in 10 mL of acetic acid and treated with bromine (0.4 mL, 8 mmol). The mixture was heated at 80° C. until the orange color was discharged (1 h). The mixture was evaporated under reduced pressure, diluted with 50 mL of ether and washed twice with 50 mL of sodium bicarbonate and then 50 mL of brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to yield 2.54 g of the title compound of Step C as a tan solid which was used immediately in the next step without further purification. 1H NMR (CDCl3): δ2.44 (s, 3H), 4.54 (s, 2H), 7.74 (d, 2H), 8.56 (d, 2H), 8.62 (s, 1H).

Workup

  1. custom(1 h)
  2. customThe mixture was evaporated under reduced pressure
  3. additiondiluted with 50 mL of ether
  4. washwashed twice with 50 mL of sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a26d8fb9353347d287dc38bb9c60ff0f
Source dataset
uspto-grants-2003_02
Patent number
US06525001B1

Reaction notes

Loading…