Bromine → HCID 90005955, compound

HRID 2175473Notes

Reaction equation

HRID 2175473 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8](=[O:17])[N:9]([CH3:16])[C:10](=[O:15])[N:11]([CH3:14])[C:12]=2[CH3:13])[CH:2]=1.[Br:19]Br>C(Cl)Cl.CC(C)=O>[Br:19][CH2:13][C:12]1[N:11]([CH3:14])[C:10](=[O:15])[N:9]([CH3:16])[C:8](=[O:17])[C:7]=1[C:3]1[CH:2]=[C:1]([CH3:18])[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 71078040HCID 71078040, compound2×

Product 1

HCID 90005955HCID 90005955, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a 25 mL 2-neck round bottom flask equipped with a condenser, addition funnel and air lock, compound 3d (1.00 g, 3.67 mmol) was dissolved in CH2Cl2 (6 mL) and held at reflux. Bromine (200 μL, 0.624 g, 3.9 mmol) was mixed with CH2Cl2 (9 mL) in the addition funnel and added dropwise to the solution of 3d at such a rate that the color was discharged between drops. The last few drops caused the reaction to stay brown. The reaction continued for 10 min before the color was discharged by the addition of a few drops of acetone. TLC showed the reaction was quantitative. The reaction was dried in vacuo and the remaining solid crystallized from 2-propanol to yield 4d (1.20 g, 93%); m.p. 136.1-137° C. 1H NMR (600 MHz, CD2Cl2) δ 7.67 (s, 1H), 7.63 (d, J=7.8, 1H), 7.45 (d, J=7.5, 1H), 7.37 (t, J=7.6, 1H), 4.22 (s, 2H), 3.60 (d, J=6.6, 3H), 3.30 (d, J=7.7, 3H), 2.41 (s, 3H). 13C NMR (151 MHz, CD2Cl2) δ 193.00, 160.95, 152.09, 149.09, 139.30, 137.77, 135.37, 130.22, 129.04, 127.11, 115.04, 31.98, 28.62, 23.75, 21.55. MS (ES+) (m/z): [M+1]+ calculated for C15H16BrN2O3, 351.03. found 350.99.

Workup

  1. customIn a 25 mL 2-neck round bottom flask equipped with a condenser, addition funnel
  2. temperatureat reflux
  3. customthe reaction
  4. customThe reaction was dried in vacuo
  5. customthe remaining solid crystallized from 2-propanol

Sources & evidence

ORD record
ord-58bdbadf237143a5a501e11489cbf7db
Source dataset
uspto-grants-2015_06
Patent number
US09062073B2

Reaction notes

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