Carbon tetrabromide → HCID 54215955, compound

HRID 1740994Notes

Reaction equation

HRID 1740994 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C@@H:22]([N:24]1[C:28]([CH3:29])=[CH:27][CH:26]=[C:25]1[CH3:30])[CH3:23].C(Br)(Br)(Br)[Br:32]>C(#N)C>[Br:32][CH2:21][C@@H:22]([N:24]1[C:28]([CH3:29])=[CH:27][CH:26]=[C:25]1[CH3:30])[CH3:23]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53738518HCID 53738518, compound

Product 1

HCID 54215955HCID 54215955, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (2.24 g, 8.50 mmol) was added in four portions over 10 minutes to an ice cooled mixture of (S)-1-(2-hydroxy-1-methylethyl)-2,5-dimethylpyrrole (1.0 g, 6.54 mmol) and carbon tetrabromide (3.03 g, 9.15 mmol) in 50 mL of acetonitrile. The mixture was stirred at 0° C. for 1.5 h, room temperature for 18 h, and 50° C. for 6 h. The solvent was removed in vacuo. The residue was purified by flash column chromatography on 70 g of silica gel, eluting with 1 L of 15% dichloromethane in hexane to give 1.22 g (85% yield) of (S)-1-(2-bromo-1-methylethyl)-2,5-dimethylpyrrole as a yellow liquid.

Workup

  1. temperaturecooled
  2. wait50° C. for 6 h
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by flash column chromatography on 70 g of silica gel
  5. washeluting with 1 L of 15% dichloromethane in hexane

Sources & evidence

ORD record
ord-2278f39eae95458eacf8621e7e5428a5
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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