Benzoyl Peroxide → 6-Bromo-3-(bromomethyl)benzofuran

HRID 2360041Notes

Reaction equation

HRID 2360041 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:5]=1[O:6][CH2:7]C(OC)=O)(=O)[CH3:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:35]N1C(=O)CCC1=O>ClC1C=CC=CC=1>[Br:16][C:13]1[CH:14]=[CH:15][C:4]2[C:1]([CH2:2][Br:35])=[CH:7][O:6][C:5]=2[CH:12]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57419482Methyl 2-(2-acetyl-5-bromophenoxy)acetate

Product 1

HCID 574194836-Bromo-3-(bromomethyl)benzofuranYield 32%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of the product from Example 88, Part C (1.0 g, 4.74 mmol) and dibenzoyl peroxide (287 mg, 1.19 mmol) in chlorobenzene (24 mL) at reflux was treated in four portions with N-bromosuccinimide (843 mg, 4.74 mmol) over 30 min. The mixture was then stirred at reflux for 2 h. The mixture was cooled, filtered and concentrated and purified by column chromatography on silica gel, eluting with 7-30% chloroform in hexanes. The procedures afforded the title compound as a light yellow oil (438 mg, 32%).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica gel
  6. washeluting with 7-30% chloroform in hexanes

Sources & evidence

ORD record
ord-86157e3b823d41a7be44ffbe82a778b5
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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