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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2103642Generated: October 29, 2026

Methyl 3-bromobenzoate → (E)-3-(2-Cyclohexyl-1-hydroxymethyl-vinyl)-benzoic acid methyl ester

https://huagongshe.com/reaction/2103642

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 3-bromobenzoateHCID 12070—
ReactantCesium fluorideHCID 25953—
Reactant(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-olHCID 67084598—
CatalystHCID 178420553HCID 178420553—
Solvent1,4-DioxaneHCID 31275—
Product(E)-3-(2-Cyclohexyl-1-hydroxymethyl-vinyl)-benzoic acid methyl esterHCID 6708469774.7%

Reaction Steps

Following the method of example 46a, Suzuki coupling of 3-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) (0.32 g, 0.28 mmol) and cesium fluoride (2.2 g, 14 mmol) in dioxane (15 mL) gives the title compound (1.0 g). MS (m/e): 257 (M+H−H2O).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07576108B2
Source datasetuspto-grants-2009_08
ORD IDord-6c6e775a4da64986b1d0d02d4755931c
Source noteuspto-grants-2009_08