HCID 20085920, compound → HCID 22998939, compound

HRID 1463178Notes

Reaction equation

HRID 1463178 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=1.4, 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, 1H, 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-e374474a715f4541814fa7a15b3c6882
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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