Benzoyl Peroxide → HCID 21268557, compound

HRID 868623Notes

Reaction equation

HRID 868623 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[C:16]3[O:15][CH2:14][CH2:13][C:12]=3[CH:11]=[C:10]([CH2:17][C:18]([OH:20])=[O:19])[CH:9]=2)=[S:7])=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:16]3[O:15][CH:14]=[CH:13][C:12]=3[CH:11]=[C:10]([CH2:17][C:18]([OH:20])=[O:19])[CH:9]=2)=[S:7])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21268558HCID 21268558, compound

Product 1

HCID 21268557HCID 21268557, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

7-(4-Methylthiobenzoyl)-2,3-dihydrobenzofuran-5-ylacetic acid (1.0 g) was heated at reflux in carbon tetrachloride (100 ml) containing n-bromosuccinimide (0.54 g) and a catalytic quantity of benzoyl peroxide. After approximately 2 hours the reaction mixture was cooled and extracted with dilute aqueous sodium carbonate. The aqueous extract was acidified with hydrochloric acid, extracted with ethyl acetate, dried and evaporated to yield a residue which was crystallized from acetone/hexane to give (7-(4-methylthiobenzoyl)benzofuran-5-ylacetic acid, m.p.--151°-153° C.

Workup

  1. temperatureAfter approximately 2 hours the reaction mixture was cooled
  2. extractionextracted with dilute aqueous sodium carbonate
  3. extractionThe aqueous extract
  4. extractionextracted with ethyl acetate
  5. customdried
  6. customevaporated
  7. customto yield a residue which
  8. customwas crystallized from acetone/hexane

Sources & evidence

ORD record
ord-4bc4742b010b4586b1ab909e5555a19e
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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