HCID 23053926, compound → HCID 22998939, compound

HRID 1650227Notes

Reaction equation

HRID 1650227 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O-:11])=O>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[Br:1][C:2]1[CH:18]=[CH:17][C:16]2[C:9](=[O:11])[C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH2:6][O:5][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 23053926HCID 23053926, compound

Product 1

HCID 22998939HCID 22998939, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideCatalyst

Procedure

A suspension of 2-(3-bromophenoxymethyl)benzoate (35 g, 0.11 mole) in 100 mL of trifluoroacetic anhydride containing 20 drops of boron trifluoride-ether complex was refluxed for 4 hours. The mixture was poured into ice-water and then extracted with diethyl ether. Concentration of ether solution under reduced pressure and chromatography of the residue on a silica gel column (Waters Associates, Prep 500) with hexane/methylene chloride (70:30) gave the pure product (14 g). m.p. 110°-112° C. pmr (CDCL3) δ: 8.10 (d, J=9.1 Hz, 1H, H1), 7.90 (dd, J=1.4, 7.6 Hz, 1H, H10) 7.57 (dt, J=1.4, 7.4, 7.4 Hz, 1H H8), 7.48 (dt, J=1.4, 7.6, 7.6 Hz, 1H, H9), 7.36 (dd, J=1.3, 7.3 Hz, 1H, H7), 7.27 (d, J=1.8 Hz, 1H, H4), 7.24 (dd, J=1.8, 9.1 Hz, 1H, H2), 5.18 (s, 2H, ArCH2O).

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-57e53e3caa0d43bf91f8f966c6882172
Source dataset
uspto-grants-1990_05
Patent number
US04923892

Reaction notes

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