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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1500460Generated: November 3, 2026

2-Bromo-1-(2-bromoethoxy)-4-methylbenzene → 5-Methyl-2,3-dihydro-1-benzofuran

https://huagongshe.com/reaction/1500460

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Bromo-1-(2-bromoethoxy)-4-methylbenzeneHCID 11033709—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
Product5-Methyl-2,3-dihydro-1-benzofuranHCID 12725190—

Reaction Conditions

Temperature-78 °C

Reaction Steps

To a solution of 2-bromo-1-(2-bromoethoxy)-4-methylbenzene (1a) (1.0 g, 3.4 mmol) in THF (20 mL) at −78° C., under N2 was added n-BuLi (2.5 M, 11 mL, 27 mmol) and the resulting mixture was stirred at −78° C., for 1 h. The mixture was quenched with saturated NH4Cl (10 mL), extracted with EtOAc (150 mL), washed with brine, dried and concentrated to give the title compound (1b) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09206166B2
Source datasetuspto-grants-2015_12
ORD IDord-a4a39f46beea4c1f884da0aef3ad7b80
Source noteuspto-grants-2015_12