Bromine → HCID 71743938, compound

HRID 2280996Notes

Reaction equation

HRID 2280996 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][N:8]=[CH:7]2.[Br:12]Br>S([O-])([O-])(=O)=O.[Ag+2].OS(O)(=O)=O>[Br:12][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:11]2[C:6]=1[CH:7]=[N:8][CH:9]=[N:10]2

Participants

5

Reactant 2

HCID 24408BromineHCID 217666758-Methylquinazoline

Product 1

HCID 71743938HCID 71743938, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 8-Methylquinazoline (10 g, 0.0694 mol) in conc.H2SO4 (100 mL), was added silver sulphate (34.64 g, 0.1111 mol) in portions at OCC. To this was added Bromine (4.4 mL, 0.0832 mol) in drops. The reaction mixture was stirred at RT for 16 h. Reaction was monitored by LCMS at regular intervals. At the end of 16 h, LCMS showed 42% starting material and 51% of product. The reaction mixture was quenched with ice and basified with NH4OH solution. The aqueous layer was extracted with EtOAc (4×500 mL), washed with water and brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum. The crude was purified by column chromatography using neutralized silica gel (60-120 mesh) and pet ether/ethyl acetate as an elutent to yield the titled compound as pale yellow liquid (51% yield). 1H NMR (DMSO-d6, 400 MHz) δ 9.60-9.58 (s, 1H), 9.40-9.38 (s, 1H), 7.93-7.91 (d, J=7.72 Hz, 1H), 7.77-7.75 (d, J=7.72 Hz, 1H), 2.62 (s, 3H).

Workup

  1. customReaction
  2. customAt the end of 16 h, LCMS
  3. customThe reaction mixture was quenched with ice
  4. extractionThe aqueous layer was extracted with EtOAc (4×500 mL)
  5. washwashed with water and brine solution
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-a8d2faddf29948d6aebba387670aa630
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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