Water → HCID 58056175, compound

HRID 1773566Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:25]2[CH:26]=[CH:27][C:22]([CH2:21][OH:20])=[CH:23][CH:24]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Nitrogen was bubbled through a mixture of 1-bromo-4-chloro-2-nitro-benzene (1.25 g, 5.3 mmol), bis(triphenylphosphine)palladium(II) chloride (90 mg, 0.13 mmol) and potassium phosphate tribasic (4.2 g, 19.7 mmol) in anhydrous 1,2-dimethoxyethane (30 mL) for 15 minutes. A solution of 4-(hydroxymethyl)phenylboronic acid (0.8 g, 5.3 mmol) in anhydrous 1,2-dimethoxyethane (1.5 mL) was added and the resulting mixture was heated at 80° C. overnight. The reaction mixture was then poured into water and extracted twice with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 70/30) to give 0.367 g of (4′-chloro-2′-nitro-biphenyl-4-yl)-methanol as a solid.

Workup

extractionextracted twice with ethyl acetate
dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe crude residue was purified by flash chromatography (hexane/EtOAc, 70/30)

Sources & evidence

ORD record: ord-5f485464040647fea0d8288050a49a08
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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