Dimethyl Sulfoxide → 2-(2-Bromophenoxy)pyrimidine

HRID 1524022Notes

Reaction equation

HRID 1524022 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].C([O-])([O-])=O.[Cs+].[Cs+].CS(C)=O>C(OCC)(=O)C>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 72442-BromophenolHCID 10796Cesium carbonateHCID 744042-Chloropyrimidine

Product 1

HCID 145311902-(2-Bromophenoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a 48 mL pressure tube containing a stirbar were added 2-chloropyrimidine (1.69 g, 14.7 mmol), 2-bromophenol (1.63 mL, 14.0 mmol), Cs2CO3 (5.49 g, 16.8 mmol) and DMSO (30 mL). The vial was sealed and heated at 120° Celsius for 15 hours. The reaction was then diluted with 100 mL of ethyl acetate and extracted with brine (2×50 mL). The organic layer was isolated, dried and concentrated to dryness to provide the crude product which was subsequently purified FCC to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 8.57 (s, 1H), 8.56 (s, 1H), 7.72-7.60 (dd, J=8.0, 1.6, 1H), 7.45-7.34 (m, 1H), 7.32-7.23 (m, 1H), 7.23-7.11 (m, 1H), 7.10-7.01 (t, J=4.8, 1H).

Workup

  1. additionTo a 48 mL pressure tube containing a stirbar
  2. customThe vial was sealed
  3. extractionextracted with brine (2×50 mL)
  4. customThe organic layer was isolated
  5. customdried
  6. concentrationconcentrated to dryness
  7. customto provide the crude product which

Sources & evidence

ORD record
ord-4354d8fb6251424faed9218dcda5e3ff
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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