2-(2-Bromophenoxymethyl)benzoic acid → 4-Bromo-6,11-dihydrodibenz[b,e]oxepin-11-one

HRID 1463180Notes

Reaction equation

HRID 1463180 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[Br:1][C:2]1[C:3]2[O:4][CH2:5][C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[C:8](=[O:10])[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 200859232-(2-Bromophenoxymethyl)benzoic acid

Product 1

HCID 151138354-Bromo-6,11-dihydrodibenz[b,e]oxepin-11-oneYield 53%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideCatalyst

Procedure

A suspension of 2-(2-bromophenoxymethyl)benzoic acid (18.8 g, 0.06 mole) in 100 mL of trifluoracetic anhydride containing ten drops of boron trifluoride-ether complex was refluxed for four hours. The mixture was poured into ice water and then extracted with diethyl ether. Concentration of the ether solution under reduced pressure gave the pure product (9.2 g), mp 127°-130° C. pmr (CDCl3) δ: 7.28-8.19 (m, 76H, aromatic H); 6.99 (t, 1H, H2); 5.30 (s, 2H, ArCH2O).

Workup

  1. temperaturewas refluxed for four hours
  2. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-5ff624106fb04c18ad7c71f656c79638
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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