Benzyl Bromide → HCID 13849544, compound

HRID 978126Notes

Reaction equation

HRID 978126 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([CH2:12][CH2:13][CH3:14])[CH:9]=[C:10]([Cl:11])[C:5]=2[O:4][C:3]=1[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([CH2:12][CH2:13][CH3:14])[CH:9]=[C:10]([Cl:11])[C:5]=2[O:4][C:3]=1[C:16]([O:18][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:17]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14579739HCID 14579739, compound

Product 1

HCID 13849544HCID 13849544, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-methyl-4-hydroxy-5-propyl-7-chloro-benzofuran-2-carboxylic acid (0.5 gm; 1.9 mmole), potassium carbonate (0.26 gm; 1.9 mmole) and benzyl bromide (0.22 ml; 1.9 mmole) in acetone (100 ml) was refluxed for a period of 2 hours. The solids were filtered off and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel and eluted with 15% ethyl acetate in hexane to yield 200 mg (30%) of benzyl 3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran-2-carboxylate, m.p. 119°-120° C.

Workup

  1. temperaturewas refluxed for a period of 2 hours
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluted with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-850f1c25e13c4f59af91b49ebcb521f2
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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