m-Chloroperbenzoic acid → HCID 57575535, compound

HRID 918804Notes

Reaction equation

HRID 918804 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:10]3[CH:11]([OH:23])[CH2:12][CH2:13][CH2:14][C:9]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 151906985-Bromo-1',2',3',4'-tetrahydro[1,1'-biphenyl]-2-ol

Product 1

HCID 57575535HCID 57575535, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the phenol and MCPBA in benzene is refluxed overnight. A solid is precipitated out and filtered. The filtrate is concentrated under vacuum and chromatographed (10% EtOAc in hexanes) to give 8-bromo-1,2,3,4-tetrahydro-dibenzofuran-4-ol 108 as clear oil, 0.66 g, 39%.

Workup

  1. customA solid is precipitated out
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under vacuum
  4. customchromatographed (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9af7dddd9d684f1da263bb500af33723
Source dataset
uspto-grants-2016_03
Patent number
US09271960B2

Reaction notes

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