4-(Trifluoromethoxy)phenylboronic acid → HCID 67486079, compound

HRID 1880570Notes

Reaction equation

HRID 1880570 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]([OH:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[F:20][C:21]([F:33])([F:32])[O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:20][C:21]([F:32])([F:33])[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:7]2[CH:16]=[C:15]([OH:17])[C:14]3[C:9]([CH:8]=2)=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 86761702HCID 86761702, compound

Product 1

HCID 67486079HCID 67486079, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

4-Hydroxy-2-naphthyl trifluoromethanesulfonate (100 mg, 0.34 mmol), 4-(trifluoromethoxy)phenyl boronic acid (0.14 g, 0.68 mmol) and Pd(PPh3)4 (20 mg, 0.017 mmol) in DME/2M K2CO3 (1/1) were heated at reflux under an argon atmosphere. After approximately 2 hours the solution was cooled and partitioned between aqueous 1N hydrochloric acid and ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. LCMS1 3.94 min. (M+H)=305

Workup

  1. temperatureat reflux under an argon atmosphere
  2. temperatureAfter approximately 2 hours the solution was cooled
  3. custompartitioned between aqueous 1N hydrochloric acid and ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-69b510ac03484fa8b719c4738182456c
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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