HCID 20085920, compound → HCID 22998939, compound

HRID 1608465Notes

Reaction equation

HRID 1608465 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]([OH: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 20085920HCID 20085920, compound

Product 1

HCID 22998939HCID 22998939, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideCatalyst

Procedure

A suspension of 2-(3-bromophenoxymethyl)benzoic acid (35 g, 0.11 mole) in 100 mL of trifluoracetic anhydride containing 20 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 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=l.4, 7.6 H, 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, H, H7), 7.27 (d, J=1.8 H, 1H, H4), 7.24 (dd, J=1.8, 9.1 Hz, 1H, H2), 5.18 (s, 2H, ARCH2O).

Workup

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

Sources & evidence

ORD record
ord-f387a2158046412e806e30f2c228b20e
Source dataset
uspto-grants-1995_03
Patent number
US05395610

Reaction notes

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