Methyl 4-bromobenzoate → HCID 67084641, compound

HRID 2103644Notes

Reaction equation

HRID 2103644 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[CH:12]1(/[CH:18]=[C:19](\B2OC(C)(C)C(C)(C)O2)/[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]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>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](/[C:19](/[CH2:20][OH:21])=[CH:18]\[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 12081Methyl 4-bromobenzoateHCID 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 67084641HCID 67084641, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following the method of example 46a, Suzuki coupling of 4-bromo-benzoic acid methyl ester (1.05 g, 4.88 mmol) with (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.48 g, 5.56 mmol) in the presence of tetrakis(triphenylphosphino)palladium(0) (0.35 g, 0.30 mmol) and cesium fluoride (2.1 g, 14 mmol) in dioxane (15 mL) gives the title compound (1.0 g). MS (m/e): 275 (M+H).

Sources & evidence

ORD record
ord-a954ad73389247bebf2329719f23413c
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

Loading…