Carbon Dioxide → 6-Bromo-2-methylthieno[3,4-d][1,3]oxazole

HRID 1624224Notes

Reaction equation

HRID 1624224 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:5](=[CH:7][S:8][CH:9]=2)[N:6]=1.C(=O)=O.[Br:13]N1C(=O)CCC1=O.[Cl-].[Na+]>O1CCCC1>[Br:13][C:9]1[S:8][CH:7]=[C:5]2[C:4]=1[O:3][C:2]([CH3:1])=[N:6]2

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 5234Sodium ChlorideHCID 67184N-bromobutanimideHCID 682422742-Methylthieno[3,4-d][1,3]oxazole

Product 1

HCID 682422956-Bromo-2-methylthieno[3,4-d][1,3]oxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 mmol of 2-methylthieno[3,4-d][1,3]oxazole was dissolved in 10 ml of tetrahydrofuran and the temperature was kept at −78° C. in a methanol bath cooled by dry ice. A solution in which 1.05 mmol of N-bromosuccinimide was dissolved in 5 ml of tetrahydrofuran was gradually added dropwise to carry out the reaction for 2 hours. Then an excess amount of saturated sodium chloride aqueous solution was added to stop the reaction. The reacted liquid was washed with water. Then the organic layer was recovered and dried under sodium sulfate. The solvent was evaporated out. The product was purified using column separation with the solvent of ethylacetate and hexane, obtaining 6-bromo-2-methylthieno[3,4-d][1,3]oxazole represented by formula (21).

Workup

  1. customthe temperature was kept at −78° C. in a methanol bath
  2. additionwas gradually added dropwise
  3. customthe reaction for 2 hours
  4. customthe reaction
  5. washThe reacted liquid was washed with water
  6. customThen the organic layer was recovered
  7. customdried under sodium sulfate
  8. customThe solvent was evaporated out
  9. customThe product was purified
  10. customcolumn separation with the solvent of ethylacetate and hexane

Sources & evidence

ORD record
ord-7f3fdd325a44432fb70c3956b9f1b2f2
Source dataset
uspto-grants-2014_07
Patent number
US08779086B2

Reaction notes

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