4-Bromoanisole → (E)-3-Cyclohexyl-2-(4-methoxy-phenyl)-prop-2-en-1-ol

HRID 2103643Notes

Reaction equation

HRID 2103643 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH:10]1(/[CH:16]=[C:17](\B2OC(C)(C)C(C)(C)O2)/[CH2:18][OH:19])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[F-].[Cs+]>O1CCOCC1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:10]1(/[CH:16]=[C:17](\[C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)/[CH2:18][OH:19])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 77304-BromoanisoleHCID 25953Cesium fluorideHCID 67084598(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 69055143(E)-3-Cyclohexyl-2-(4-methoxy-phenyl)-prop-2-en-1-olYield 58.3%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following the method of example 46a, Suzuki coupling of 1-bromo-4-methoxy-benzene (0.65 g, 3.48 mmol) with (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) -prop-2-en-1-ol (1.05 g, 3.94 mmol) in the presence of tetrakis(triphenylphosphino)palladium(0) (0.25 g, 0.22 mmol) and cesium fluoride (1.69 g, 11 mmol) in dioxane (20 mL) gives the title compound (0.5 g). 1H-NMR (CDCl3) δ=0.92-2.15 (m, 10H), 2.62-2.77 (m, 1H), 3.82 (s, 3H), 4.23-4.29 (m, 2H), 6.02-6.11 (m, 1H), 6.86-6.94 (m, 2H), 7.11-7.17 (m, 2H).

Sources & evidence

ORD record
ord-a0557240c00f4791a4504bfc8410398b
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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