3,5-Dichlorobenzylic alcohol → 2,6-Dichloro-2′,4′-difluoro[1,1′-biphenyl]-4-methanol

HRID 402840Notes

Reaction equation

HRID 402840 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1B(O)O.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([Cl:22])[C:20]=1I)[CH2:16][OH:17].ClC1C=C(C=C(Cl)C=1)CO>>[Cl:12][C:13]1[CH:14]=[C:15]([CH2:16][OH:17])[CH:18]=[C:19]([Cl:22])[C:20]=1[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 432363,5-Dichlorobenzylic alcoholHCID 27343342,4-Difluorophenylboronic acidHCID 66764840HCID 66764840, compound

Product 1

HCID 674713032,6-Dichloro-2′,4′-difluoro[1,1′-biphenyl]-4-methanolYield 72.5%

Procedure

Using essentially the same coupling procedure as for Example 8-1, Step 1, but heating 2,4-difluorophenylboronic acid (456 mg, 2.89 mmol) and 3,5-dichloro-4-iodobenzyl alcohol (350 mg, 1.155 mmol) in a microwave at 115° C. for 120 minutes, afforded the title intermediate (242 mg) without formation of any appreciable 3,5-dichlorobenzyl alcohol.

Sources & evidence

ORD record
ord-4e5d3bee6e4b468ba2407a65071734d1
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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