5-Fluoro-2-methoxyphenylboronic acid → 3',5-Difluoro-2-methoxy-4'-(phenylsulfonyl)biphenyl

HRID 1963664Notes

Reaction equation

HRID 1963664 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[C:4]([F:17])[CH:3]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([O:28][CH3:29])=[C:23](B(O)O)[CH:24]=1>C1(C)C=CC=CC=1.C(O)C.C([O-])([O-])=O.[Na+].[Na+].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:17][C:4]1[CH:3]=[C:2]([C:21]2[CH:20]=[C:19]([F:18])[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])[CH:7]=[CH:6][C:5]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

8

Reactant 2

HCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 673740874-Bromo-2-fluoro-1-(phenylsulfonyl)benzene

Product 1

HCID 672389663',5-Difluoro-2-methoxy-4'-(phenylsulfonyl)biphenyl

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution/suspension of the product from part (i) (0.55 g), 5-fluoro-2-methoxy-phenylboronic acid (0.3 g) in toluene (6 ml), ethanol (4 ml) and 2M Na2CO3 (3 ml) was added tetrakis(triphenylphosphine)palladium (0.05 g). The mixture was heated to 85° C. for 3 h, concentrated under reduced pressure to give a crude material. The residue was suspended in water, extracted with ethylacetate, washed with brine, dried (MgSO4) and concentrated under reduced pressure. Purification using flash column chromatography (eluent 10% diethylether/hexane) gave the subtitle compound, yield 0.39 g.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a crude material
  3. extractionextracted with ethylacetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-5d85ede537cd4c4d852569b83912f4a2
Source dataset
uspto-grants-2013_04
Patent number
US08415394B2

Reaction notes

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