Bromine → Methyl 4-(bromomethyl)-2-hydroxybenzoate

A refluxing solution of 4-methylsalicylic acid methyl ester (5.1 g, 31.3 mmol) in carbon tetrachloride (50 mL) was treated dropwise with a solution of bromine (1.6 mL, 31.3 mmol) in carbon tetrachloride (5 mL) while under illumination by a 200 W incandescent light bulb. The reaction mixture was stirred for an additional 30 min at reflux and concentrated in vacuo. The residue was dissolved in EtOAc (50 mL) and washed with aqueous sodium thiosulfate (5%, 50 mL), water (50 mL), and brine (50 mL). The organic layer was dried over Na2SO4, concentrated, and the product 4-bromomethylsalicylic acid methyl ester was isolated by recrystallization from heptane (1.6 g, 21%).

1. temperatureat reflux
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in EtOAc (50 mL)
4. washwashed with aqueous sodium thiosulfate (5%, 50 mL), water (50 mL), and brine (50 mL)
5. dry with materialThe organic layer was dried over Na2SO4
6. concentrationconcentrated

ORDレコード

ord-4288fd434a91404191e1d4f368ec1d60

出典データセット

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08242115B2