Allyl bromide → 2'-Allyloxy-2,4-dichloro-6'-fluorobiphenyl

HRID 902381Notes

Reaction equation

HRID 902381 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([OH:16])=[CH:11][CH:12]=[CH:13][C:14]=1[F:15].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CS(C)=O>[CH2:25]([O:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 691181582',4'-Dichloro-6-fluoro-biphenyl-2-ol

Product 1

HCID 691171992'-Allyloxy-2,4-dichloro-6'-fluorobiphenylYield 92.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Treatment of 2′,4′-dichloro-6-fluorobiphenyl-2-ol (1.6 g, 6.2 mmol) with potassium carbonate (1.3 g, 9.3 mmol) and allyl bromide (0.79 mL, 9.3 mmol) in DMSO (50 mL) according to the procedure described for Example 69, Step 3 provided 1.7 g (92%) of 2′-allyloxy-2,4-dichloro-6′-fluorobiphenyl as a pale yellow oil.

Sources & evidence

ORD record
ord-54f17654ded54c1cbfed12a2fda8190e
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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