Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 412747Generated: October 26, 2026

4-(2-Bromophenyl)-2-methyl-2-butanol → 2,2-Dimethylchroman

https://huagongshe.com/reaction/412747

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-(2-Bromophenyl)-2-methyl-2-butanolHCID 15247164—
ReactantSodium t-butoxideHCID 23676156—
Catalyst(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumHCID 6505921—
SolventTolueneHCID 1140—
Product2,2-DimethylchromanHCID 13693693%

Reaction Steps

A 4 mL vial was charged with 4-(2-bromophenyl)-2-methyl-2-butanol (97 mg, 0.40 mmol), Pd(dba)2 (11.5 mg, 0.02 mmol), Ph5FcP(t-Bu)2 (14.2 mg, 0.02 mmol) and sodium t-butoxide (46 mg, 0.48 mmol). Anhydrous toluene (2 mL) was added into the vial, and the vial was sealed with a cap containing a PTFE septum and removed from the drybox. The reaction mixture was stirred at room temperature for 10 min. The reaction solution was adsorbed onto silica gel and isolated by eluting with 5% ethyl acetate in hexanes to give 60 mg (93%) of 2,2-dimethylchroman as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06562989B2
Source datasetuspto-grants-2003_05
ORD IDord-c5bdc0ef855d42d0a63794e693c19dc3
Source noteuspto-grants-2003_05