Water → 4-Fluoro-2-(3-furanyl)-6-methylphenol

HRID 63379Notes

Reaction equation

HRID 63379 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[O:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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]>[F:8][C:6]1[CH:5]=[C:4]([CH3:9])[C:3]([OH:10])=[C:2]([C:13]2[CH:14]=[CH:15][O:11][CH:12]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 198108992-bromo-4-fluoro-6-methylphenol

Product 1

HCID 900021994-Fluoro-2-(3-furanyl)-6-methylphenolYield 41.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

2-bromo-4-fluoro-6-methylphenol (337 mg, 1.20 mmol), 3-furanylboronic acid (162 mg, 1.45 mmol), Pd(dppf)Cl2 (98.3 mg, 0.12 mmol) and sodium carbonate (383 mg, 3.61 mmol) were dissolved in DME:water=20 mL:10 mL, followed by stirring in microwave at 120° C. for 20 minutes. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and purified by column chromatography (silica gel; hexane/ethyl acetate, 9/1) to obtain 4-fluoro-2-(furan-3-yl)-6-methylphenol (96 mg, 30%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by column chromatography (silica gel; hexane/ethyl acetate, 9/1)

Sources & evidence

ORD record
ord-4af0792f705347d9a7e7ca3dc00e4a31
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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