Water → 5-Chloro-4'-fluoro-2-nitrobiphenyl

HRID 238956Notes

Reaction equation

O.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7](B(O)O)[CH:8]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>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.C(OCC)(=O)C.C(COC)OC>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To water (2 mL) and dimethoxyethane (20 mL), 5-chloro-2-nitrophenylboronic acid (3.27 g, 16.4 mmol), 1-fluoro-4-iodobenzene (3.65 g, 16.4 mmol), tetrakis(triphenylphosphine)palladium (0.95 g, 0.82 mmol) and potassium carbonate (6.81 g, 49.3 mmol) were added, and the mixture was stirred under a nitrogen atmosphere at 60° C. for 2 hours. After the reaction, the reaction mixture was cooled to room temperature and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL) and saturated brine (20 mL), it was dried with sodium sulfate. The solvent was distilled off under reduced pressure to give 5-chloro-4′-fluoro-2-nitrobiphenyl as a crude product. The obtained compound was used for the subsequent reaction without further purification.

Workup

customAfter the reaction
temperaturethe reaction mixture was cooled to room temperature
washAfter the organic phase was washed with water (30 mL) and saturated brine (20 mL), it
dry with materialwas dried with sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-986e687770ec4c148b252687f7dae3f4
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642640B2

Reaction notes

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