Dimethylformamide → 3-Bromo-2-methylbenzaldehyde

Temperature

-78 °C

To a solution of 1,3-dibromo-2-methylbenzene (3 g, 12.00 mmol) in Tetrahydrofuran (THF) (100 mL) stirred under nitrogen at −78° C. was added BuLi (9.00 mL, 14.40 mmol) dropwise. The reaction mixture was stirred at −78° C. for 20 min. DMF (1.115 mL, 14.40 mmol) was added dropwise. The reaction mixture was continuously stirred for 2 hours. The reaction was quenched with sat. aq. ammonia chloride solution. The aqueous layers were separated and extracted by EA for 3 times. The combined organic layers were washed by brine, dried over anhydrous sodium sulfate. The dried solution was concentrated in vacuo to afford 3-bromo-2-methylbenzaldehyde (D93) (2.4 g), which was used for the next step without further purification. MS (ES): C8H7BrO requires 197.9. found 199 (M+H+)

1. stirringThe reaction mixture was continuously stirred for 2 hours
2. customThe reaction was quenched with sat. aq. ammonia chloride solution
3. customThe aqueous layers were separated
4. extractionextracted by EA for 3 times
5. washThe combined organic layers were washed by brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationThe dried solution was concentrated in vacuo

ORD record

ord-e6d134a44706443eb092f147e4517bfa

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2