Diisobutylaluminum hydride → 2-Bromo-5-methylbenzaldehyde

Temperature

-78 °C

Step AI (2): 2-Bromo-N-methoxy-N,5-dimethylbenzamide (656 mg, 2.54 mmol) was dissolved in THF (20 mL). The reaction mixture was cooled down to −78° C. and a 1.0M solution of DIBAL-H (7.62 mL, 7.62 mmol) was added. The reaction mixture was stirred at −78° C. for 1 h. The reaction was quenched with acetone and stirred at rt with Rochelle's salt. The mixture was extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum to yield 2-bromo-5-methylbenzaldehyde (500 mg, 99%) as a colorless oil. LC-MS (M+H)+=199.21.

1. customThe reaction was quenched with acetone
2. stirringstirred at rt with Rochelle's salt
3. extractionThe mixture was extracted with DCM
4. dry with materialThe combined organic phases were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuum

ORD record

ord-6006656d4a0b46e5a31a75ba3e62c9e5

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772221B2