2-Bromopropane → HCID 21243568, compound

HRID 621801Notes

Reaction equation

HRID 621801 reaction equation
[Br:1][C:2]1[C:3]([OH:19])=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1[Br:7].[CH3:20][C:21](C)([O-])[CH3:22].[K+].BrC(C)C>CS(C)=O>[Br:1][C:2]1[C:3]([O:19][CH:21]([CH3:22])[CH3:20])=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 23665647Potassium tert-butoxideHCID 54697149HCID 54697149, compound

Product 1

HCID 21243568HCID 21243568, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 4,5-dibromo-3-hydroxy-1-phenyl-1H-pyrrole-2-carboxylate (4.0 g, 0.010 moles) is dissolved in DMSO (20 mL) under argon. Potassium tert-butoxide (1.2 g, 0.011 moles) is added, followed after 15 minutes by 2-bromopropane (2.6 g, 0.021 moles), and the mixture is stirred at room temperature. After 24 hours the mixture is stirred into ice water (300 mL) and extracted with CH2Cl2 (3×125 mL). The combined extracts are washed with saturated brine (2×100 mL) and dried over MgSO4. Removal of the solvent under reduced pressure left the product (4.1 g) as an oil, sufficiently pure for further use.

Workup

  1. extractionextracted with CH2Cl2 (3×125 mL)
  2. washThe combined extracts are washed with saturated brine (2×100 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent under reduced pressure
  5. waitleft the product (4.1 g) as an oil

Sources & evidence

ORD record
ord-86459fa50ea64726b151ea778922188b
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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