Potassium Acetate → HCID 57882761, compound

HRID 1715497Notes

Reaction equation

HRID 1715497 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=2)[CH:3]=1.[B:16]1(B2OC(C)(C)C(C)(C)O2)[O:20]C(C)(C)C(C)(C)[O:17]1.C([O-])(=O)C.[K+]>CS(C)=O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:13][C:12]([F:15])([F:14])[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([B:16]([OH:20])[OH:17])[CH:11]=[CH:10]2

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 67482669HCID 67482669, compound

Product 1

HCID 57882761HCID 57882761, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-6-(trifluoromethyl)-naphthalene (50 mg, 0.182 mmol), bis(pinacolato)diboron (92 mg, 0.362 mmol), and potassium acetate (53 mg, 0.540 mmol) were suspended in 2.5 mL of methyl sulfoxide. The mixture was de-oxygenated by four vacuum-nitrogen fill cycles, and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (3.7 mg, 0.0045 mmol) added, and the resultant mixture heated at 80° C. under a nitrogen atmosphere for 1 h. The mixture was cooled, diluted with ethyl acetate, and washed successively with two portions of water and one portion of brine. The organic layer was dried over magnesium sulfate, concentrated in vacuo, and the residue suspended in a mixture of 10 mL of acetone and 2 mL of aqueous 2N hydrochloric acid. The resultant mixture was heated at 60° C. for 16 hours and the crude boronic acid purified by reverse phase HPLC to give [6-(trifluoromethyl)-2-naphthyl]boronic acid as a white powder. 1H NMR (500 MHz, DMSO) δ: 8.47 (s, 1H); 8.38 (s, 1H); 8.33 (br s, 2H); 8.14 (d, J=8.7 Hz, 1H); 8.07 (d, J=8.2 Hz, 1H); 8.00 (d, J=8.2 Hz, 1H); 7.73 (dd, J=1.6, 8.5 Hz, 1H).

Workup

  1. additionadded
  2. temperatureThe mixture was cooled
  3. washwashed successively with two portions of water and one portion of brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionthe residue suspended in a mixture of 10 mL of acetone and 2 mL of aqueous 2N hydrochloric acid
  7. customthe crude boronic acid purified by reverse phase HPLC

Sources & evidence

ORD record
ord-88f6284947a948a5a53c7823c04197ff
Source dataset
uspto-grants-2010_09
Patent number
US07799818B2

Reaction notes

Loading…