Potassium Phosphate, Tribasic → 4-Fluoro-3-nitro-1,1'-biphenyl

HRID 2273601Notes

Reaction equation

HRID 2273601 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 106802714-Fluoro-3-nitro-1,1'-biphenylYield 92.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Dioxane is added under a nitrogen atmosphere to a mixture of 4-bromo-1-fluoro-2-nitrobenzene (220 mg, 1.00 mmol), benzeneboronic acid (143 mg, 1.20 mmol), potassium phosphate (636 mg, 3.00 mmol) and Tetrakis(triphenylphosphine)-palladium(0) (55 mg, 0.05 mmol). The reaction may be heated to an appropriate temperature such as 90° C., stirred for an appropriate time, such as overnight, and filtered. The filtrate may be concentrated and purified by Biotage column chromatography to give 4-fluoro-3-nitrobiphenyl (200 mg).

Workup

  1. customThe reaction
  2. filtrationfiltered
  3. concentrationThe filtrate may be concentrated
  4. custompurified by Biotage column chromatography

Sources & evidence

ORD record
ord-3f217b9bbf48414f85d0e96717f28c9c
Source dataset
uspto-grants-2015_09
Patent number
US09125901B2

Reaction notes

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