Diisobutylaluminum hydride → 3-Bromo-4-iodobenzenemethanol

Temperature

-78 °C

A solution of methyl 3-bromo-4-iodobenzoate (4.3 g, 12.6 mmol) in CH2Cl2 was cooled, under N2, to −78° C. DIBAL-H (25.2 mL of a 1M solution in CH2Cl2) was added slowly to the solution, which was stirred at −78° C. for 45 minutes and then allowed to come to room temperature. Next, the reaction mixture was diluted with 1M HCL (40 mL) and stirred for 30 minutes. The reaction was further diluted with water and extracted with CH2Cl2. The organic phase was dried (Na2SO4) and concentrated under vacuum to afford the intermediate (3.2 g, 82%) as a solid. 1HNMR (CDCl3) δ ppm: 7.85 (1H), 7.67 (1H), 7.02 (1H), 4.65 (2H), 1.76 (1H, OH).

1. customto come to room temperature
2. additionNext, the reaction mixture was diluted with 1M HCL (40 mL)
3. stirringstirred for 30 minutes
4. extractionextracted with CH2Cl2
5. dry with materialThe organic phase was dried (Na2SO4)
6. concentrationconcentrated under vacuum

ORD record

ord-1cddb84de3a7458ca3009acaffd8d623

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466115B2