1-Indanone → 1-Indanone, 6-bromo-

HRID 2220197Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:14])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1.[Br:15]Br>Cl>[Br:15][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][C:5]2=[O:14])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 3-neck 250 mL round bottom flask equipped with a mechanical stirrer and charged with anhydrous aluminum chloride (16.6 gm, 0.125 mole) was added indanone (6.6 gm, 0.05 mole) in-two portions over 3 minutes. The reaction mixture was stirred for 10 minutes before bromine (9.7 g, 0.06 mole) was added dropwise over 10 minutes. The reaction mixture was heated to 80° C. for 5 minutes. The resulting mixture was poured into a mixture of ice (100 g) and concentrated HCl (20 mL). The resulting mixture was extracted with ether. The ether layer was separated, washed with water, dried (Na2SO4), filtered and concentrated. The crude material was purified by flash chromatography over silica gel eluting with 15% ether/hexanes to afford 6-Bromo-indan-1-one(2.0g, 19%). 1HNMR(CDCl3) δ 7.81 (d, 1H, J=1.76 Hz),7.62 (dd, 1H, J=8.36, 2.20 Hz), 7.30 (d, 1H, J=8.30 Hz), 3.03 (t, 2H, J=6.16 Hz), 2.65 (t, 2H, J=6.20 Hz). HPLC Rt=3.09 min.

Workup

customTo a 3-neck 250 mL round bottom flask equipped with a mechanical stirrer
additionwas added dropwise over 10 minutes
extractionThe resulting mixture was extracted with ether
customThe ether layer was separated
washwashed with water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by flash chromatography over silica gel eluting with 15% ether/hexanes

Sources & evidence

ORD record: ord-f77ae52dd8da409baa5566f6718a8cd5
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417040B2

Reaction notes

Loading…