Cyclohexanol → 1-Bromo-2-chloro-3-(cyclohexyloxy)benzene

Reaction equation

C1(O)CCCCC1.CN(C)[C:10]1[CH:11]=[C:12](CO)[CH:13]=[CH:14][CH:15]=1.[Br:19][C:20]1[C:21]([Cl:27])=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.CC1(C)C(C)(C)OB(C2C=NNC=2)O1>>[Br:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:21]=1[Cl:27]

Participants

Reactant 4

HCID 7966Cyclohexanol

HCID 90133m-(Dimethylamino)benzyl alcohol

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HCID 64552373-Bromo-2-chlorophenol

Product 1

HCID 866813101-Bromo-2-chloro-3-(cyclohexyloxy)benzene

Procedure

The title compound was prepared by substituting for cyclohexanol for (3-(dimethylamino)phenyl)methanol and 3-bromo-2-chlorophenol for 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole in EXAMPLE 34A.

Sources & evidence

ORD record: ord-7b7a266fb2ea4129a841d2038f9a6dc1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266877B2

Reaction notes

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