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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490748Generated: October 26, 2026

2-Methoxybenzylamine, N-trifluoroacetyl- → HCID 178486938, compound

https://huagongshe.com/reaction/1490748

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Methoxybenzylamine, N-trifluoroacetyl-HCID 62491258—
ReagentBis(pinacolato)diboraneHCID 2733548—
Reagent4,4'-Di-tert-butyl-2,2'-bipyridylHCID 4249187—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178486938HCID 17848693839%
ProductHCID 178488281HCID 17848828120%

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 dtbpy (2.0 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 1:2 meta:para borylation in 70% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound (as a 1:2 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (53.1 mg, 0.15 mmol, 59%).

Provenance & Evidence

DOI10.1002/anie.201708967
Source datasetBorylation dataset from Roche
ORD IDord-77a974ad7b754ffb94b6a3f6496ee1e6
Source noteBorylation dataset from Roche