Hydrochloric Acid → HCID 57882765, compound

HRID 1817752Notes

Reaction equation

HRID 1817752 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH:3]=1.[B:17]1(B2OC(C)(C)C(C)(C)O2)[O:21]C(C)(C)C(C)(C)[O:18]1.CC([O-])=O.[K+].N#N.Cl>CS(C)=O.CCCCCC.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].CC(C)=O>[F:14][C:13]([F:16])([F:15])[O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([B:17]([OH:21])[OH:18])[CH:11]=[CH:10]2

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 57429270HCID 57429270, compound

Product 1

HCID 57882765HCID 57882765, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 180AcetoneSolventHCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-6-(trifluoromethoxy)naphthalene (428 mg, 1.47 mmol), bis(pinacolato)diboron (410 mg, 1.62 mmol), and KOAc (433 mg, 4.41 mmol) were suspended in DMSO (12 ml). The mixture was de-oxygenated by vacuum-N2 fill cycles, followed by the addition of catalyst PdCl2(dppf) (30 mg, 2.5 mol %). The reaction was heated under N2 atmosphere to 80° C. for 2 hr. The reaction was diluted with hexane (100 ml), washed with water, brine, and dried over Na2SO4. After evaporation of solvent, the residue obtained was treated with acetone (20 ml) and 2N HCl (5 ml) for 24 h. The crude boronic acid was purified by reverse phase HPLC to give [6-(trifluoromethoxy)-2-naphthyl]boronic acid as a white powder. NMR (500 MHz, CDCl3) δ: 7.44 (dd, J=2.3, 9.0 Hz, 1H); 7.74 (br s, 1H); 7.98 (d, J=8.2 Hz, 1H); 8.11 (d, J=9.0 Hz, 1H); 8.35 (dd, J=1.1 8.2 Hz, 1H); 8.85 (br s, 1H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. customAfter evaporation of solvent
  4. customthe residue obtained
  5. customThe crude boronic acid was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-31a731f5bbc64bffb9e9855bd37f8de6
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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