Water → 4-Bromo-3'-Fluoro-3-Methoxy-1,1'-Biphenyl

HRID 528588

Reaction equation

HRID 528588 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].[F:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C(Cl)Cl.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].C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([F:11])[CH:17]=2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27339863-Fluorophenylboronic acidHCID 121872021-Bromo-4-iodo-2-methoxybenzene

Product 1

HCID 897620844-Bromo-3'-Fluoro-3-Methoxy-1,1'-Biphenyl

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of PdCl2(dppf)-CH2Cl2 adduct (0.065 g, 0.080 mmol), 1-bromo-4-iodo-2-methoxybenzene (CombiBlocks, 0.250 g, 0.799 mmol), 3-fluorophenylboronic acid (0.123 g, 0.879 mmol) and potassium phosphate (0.848 g, 3.99 mmol) in dioxane (2.130 ml)/water (1.065 ml) was heated to 90° C. overnight. The reaction was diluted with DCM and separated from the aqueous via phase separator (Radleys Discovery Technologies). After concentration in vacuo, the material was purified via MPLC (12-g Redi Sep Gold), eluting with 0-100% ethyl acetate in heptanes to yield, after concentration, 4-bromo-3′-fluoro-3-methoxy-1,1′-biphenyl as an orange oil, which was used without further purification.

Workup

  1. customseparated from the aqueous via phase separator (Radleys Discovery Technologies)
  2. concentrationAfter concentration in vacuo
  3. customthe material was purified via MPLC (12-g Redi Sep Gold)
  4. washeluting with 0-100% ethyl acetate in heptanes
  5. customto yield
  6. concentrationafter concentration, 4-bromo-3′-fluoro-3-methoxy-1,1′-biphenyl as an orange oil, which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-a2cb8c1e3c1c4b5f8dc08dffba635e8a
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Linked notes

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