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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2209290Generated: October 30, 2026

Methyl iodide → 7-Bromo-1,4,4-trimethyl-3,1-benzoxazin-2-one

https://huagongshe.com/reaction/2209290

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium bis(trimethylsilyl)amideHCID 2724254—
Reactant7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-oneHCID 46856486—
SolventDimethylformamideHCID 6228—
SolventTetrahydrofuranHCID 8028—
Product7-Bromo-1,4,4-trimethyl-3,1-benzoxazin-2-oneHCID 117843176—

Reaction Steps

Into the solution of 7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.37 (1.35 g) in DMF (20 mL) was added 1M solution of NaHMDS in THF (7 mL) at rt. After 30 min., MeI (0.85 g) was added. After overnight stirring, the reaction mixture was extracted with ethyl acetate and washed with brine, and dried with dry agent. After removal of the solvent, the residue was crystallized from mixture of DCM and Hexane to provide 1.2 g of 7-bromo-1,4,4-trimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.38 was synthesized.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09376441B2
Source datasetuspto-grants-2016_06
ORD IDord-6f60589751744e599d97717392b38cd7
Source noteuspto-grants-2016_06