5-Bromo-1-indanone → (5-Bromo-2,3-dihydro-1H-inden-2-yl)methanol

A solution of Ethyl 5-bromo-2,3-dihydro-1H-indene-2-carboxylate (prepared from 5-Bromo-2,3-dihydro-1H-inden-1-one, following similar procedure of US2005/0075366, compound 148) in 100 mL of anhydrous THF was added LiAlH4 (4.94 g, 130 mmol) portionwise at 0° C. The mixture was warmed slowly to RT and stirred overnight. The reaction mixture was quenched with water (5 mL) and diluted with EtOAc (200 mL) and then filtered. The filtrate was washed with water (300 mL) and brine (300 mL), dried over Na2SO4 and concentrated to dryness to obtain the title compound. 1H-NMR (300 MHz, CDCl3) δ 7.33 (s, 1H), 7.24 (d, J=7.9 Hz, 1H), 7.06 (d, J=7.9 Hz, 1H), 3.64 (d, J=6.4 Hz, 2H), 2.96-3.09 (m, 2H), 2.65-2.77 (m, 3H).

1. customThe reaction mixture was quenched with water (5 mL)
2. additiondiluted with EtOAc (200 mL)
3. filtrationfiltered
4. washThe filtrate was washed with water (300 mL) and brine (300 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated to dryness

ORD record

ord-7fe056810aa6497d9224e0e13ccffb59

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999990B2