Hydrochloric Acid → 3-Bromo-2-hydroxybenzaldehyde

To a 500 mL 3-neck round flask, paraformaldehyde (5.96 g, 199 mmol), and 12.60 g of anhydrous MgCl2 (12.60 g, 132 mmol) was added in acetonitrile (300 mL). Then 13.40 g of triethylamine was introduced slowly at room temperature. The mixture was stirred at room temperature for 20 min. 2-bromophenol (11.45 g, 66.2 mmol) was added to the above mixture. Then the reaction mixture was refluxed overnight. Then the mixture was cooled to room temperature, HCl (3N, 150 mL) were added to dilute the mixture. The resulted mixture was filtered through celite, and washed with tertbutyl methyl ether (200 mL). The organic solution was washed with 1N HCl (100 mL×2). The combined acid phase was extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine (100 mL×2), water (100 mL×2), dried over sodium sulphate and concentrated to give 3-bromo-2-hydroxybenzaldehyde (D98) (2.1 g) as yellow oil, which was directly used in next step. MS (ES): C7H5BrO2 requires 199.9. found 201.0 (M+H+).

1. temperatureThen the reaction mixture was refluxed overnight
2. temperatureThen the mixture was cooled to room temperature
3. additionto dilute the mixture
4. filtrationThe resulted mixture was filtered through celite
5. washwashed with tertbutyl methyl ether (200 mL)
6. washThe organic solution was washed with 1N HCl (100 mL×2)
7. extractionThe combined acid phase was extracted with EtOAc (100 mL×2)
8. washThe combined organic layers were washed with brine (100 mL×2), water (100 mL×2)
9. dry with materialdried over sodium sulphate
10. concentrationconcentrated

ORD record

ord-6ceb1c7a307e4adeb4a8c062bb651206

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2