2-Bromopropane → HCID 58149895, compound

HRID 2192488Notes

Reaction equation

HRID 2192488 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 58149895HCID 58149895, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-chloro-4-hydroxybenzoate (Acros Organics; 0.2 g, 1.072 mmol) was stirred with 2-bromopropane (0.201 ml, 2.144 mmol) and potassium carbonate (296 mg, 2.144 mmol) in DMF (2 ml) at 100° C. for 1.5 hr. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under vacuum and the residue was purified by Mass-Directed Auto-Preparative HPLC (formic acid modifier) to give the title compound as a yellow oil (150 mg).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was purified by Mass-Directed Auto-Preparative HPLC (formic acid modifier)

Sources & evidence

ORD record
ord-1595efa900964a9da2a5e4e902c9f8f2
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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