HCID 23346467, compound → HCID 23346443, compound

HRID 1856276Notes

Reaction equation

HRID 1856276 reaction equation
C1CNC(=O)C1.[Br:7][Br-]Br.[C:10]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]2([CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:14]=1)(=[O:12])[CH3:11]>O1CCCC1.S(=O)(=O)(O)O>[Br:7][CH2:11][C:10]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]2([CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:14]=1)=[O:12]

Participants

4

Reactant 1

HCID 23346467HCID 23346467, compound

Product 1

HCID 23346443HCID 23346443, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidone hydrotribromide [(pyrrolidone)3HBr3 ] is added at about 20° C. to the ketone from step (b) (12 g) in tetrahydrofuran (1500 ml) containing 10 drops of concentrated sulphuric acid. The mixture is stirred for 24 hours. Precipitated salts are removed by filtration and the filtrate is concentrated to a small volume. Water (200 ml) is added and the mixture is extracted three times with diethyl ether. After drying the solvent is evaporated, yielding a semi-crystalline residue. Crystallization from methanol gives the pure bromoacetyl title compound, m.p. 75°-77° C.

Workup

  1. customPrecipitated salts are removed by filtration
  2. concentrationthe filtrate is concentrated to a small volume
  3. additionWater (200 ml) is added
  4. extractionthe mixture is extracted three times with diethyl ether
  5. customAfter drying the solvent
  6. customis evaporated
  7. customyielding a semi-crystalline residue
  8. customCrystallization from methanol

Sources & evidence

ORD record
ord-3f07d6b6bb154daebb6878af167f1240
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

Loading…