Heptane → 5-Fluoro[1,1'-biphenyl]-3-ol

HRID 1820694Notes

Reaction equation

HRID 1820694 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6](I)[CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].CCCCCCC>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 8900HeptaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 668822513-fluoro-5-iodophenol

Product 1

HCID 233702025-Fluoro[1,1'-biphenyl]-3-olYield 94.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

Palladium (II) acetate (2.4 mg, 0.01 mmol) was added to a suspension of 3-fluoro-5-iodophenol (250 mg, 1.05 mmol), phenylboronic acid (154 mg, 1.26 mmol) and sodium carbonate (3.34 g, 3.15 mmol) in water (5 mL), under an atmosphere of nitrogen. The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was then filtered through a plug of dicalite to remove black precipitate. The dicalite was washed with MeOH. The filtrate was diluted with water (250 mL) and then adjusted to pH2 using 2M HCl (aq). The product was extracted into DCM, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by chromatography on silica gel. Elution with 10:90 ethyl acetate:heptane afforded 5-fluorobiphenyl-3-ol (186 mg, 0.988 mmol, 94%) M.S. (ESI) (m/z): 187 [M−H]−.

Workup

  1. filtrationThe reaction mixture was then filtered through a plug of dicalite
  2. customto remove black precipitate
  3. washThe dicalite was washed with MeOH
  4. additionThe filtrate was diluted with water (250 mL)
  5. extractionThe product was extracted into DCM
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by chromatography on silica gel
  9. washElution with 10:90 ethyl acetate

Sources & evidence

ORD record
ord-cd374df37ecc449095d262a3e521f9cd
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

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