Water → 2-Allyloxy-2',6'-dichloro-5-fluorobiphenyl

HRID 902321Notes

Reaction equation

HRID 902321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:10]([OH:16])=[CH:11][CH:12]=[C:13]([F:15])[CH:14]=1.[CH2:17](Br)[CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:19]([O:16][C:10]1[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=1[C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])[CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 691179112',6'-Dichloro-5-fluorobiphenyl-2-ol

Product 1

HCID 691175262-Allyloxy-2',6'-dichloro-5-fluorobiphenylYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′,6′-dichloro-5-fluorobiphenyl-2-ol (11.63 g, 45 mmol) in DMF (150 mL) was added allyl bromide (5.8 mL, 67.5 mmol) and potassium carbonate (18.6 g, 135 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight and poured into water. The mixture was extracted with methylene chloride and washed with water. The solvent was removed under vacuum. Chromatography with 0–30% ethyl acetate in hexanes afforded 12.7 g (94%) of 2-allyloxy-2′,6′-dichloro-5-fluorobiphenyl as a light yellow oil. MS (EI) m/z 296 (M+).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. washwashed with water
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3de75cc78a1440c1820744a854ff5763
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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