Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490747Generated: October 26, 2026

2-Methoxybenzylamine, N-trifluoroacetyl- → HCID 178488281, compound

https://huagongshe.com/reaction/1490747

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Methoxybenzylamine, N-trifluoroacetyl-HCID 62491258—
ReagentBis(pinacolato)diboraneHCID 2733548—
ReagentTetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateHCID 165587889—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178486938HCID 17848693848%
ProductHCID 178488281HCID 17848828149%

Reaction Conditions

Temperature50 °C

Reaction Steps

Following general procedure F using 2,2,2‐Trifluoro‐N‐(2‐methoxybenzyl)acetamide (58.3 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1:1 meta:para borylation in 97% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound (as a 1:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (87.4 mg, 0.24 mmol, 97%).

Provenance & Evidence

DOI10.1002/anie.201708967
Source datasetBorylation dataset from Roche
ORD IDord-1751b0c7cc5c46e2935c82d2dbb2e1d2
Source noteBorylation dataset from Roche