Tetra-n-butylammonium tribromide → HCID 58764135, compound

A solution of tetrabutyl ammonium tribromide (9.9 g, 20.5 mmol) in CHCl3 (60 mL) was added to a stirred solution of 5-ethoxy-2-ethyl-phenol (3.1 g, 18.6 mmol) dissolved in CHCl3 (90 mL). The reaction mixture was stirred for 30 mins and then quenched with 5% solution of sodium thiosulfate (30 mL). The biphasic mixture was stirred for 30 mins and then the layers were separated. The organic layer was washed with 1 N HCl, brine, dried over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 15% EtOAc in hexanes) gave the product as an oil (2.6 g, 58%). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3 H), 1.44 (t, J=7.1 Hz, 3 H), 2.53 (q, J=7.6 Hz, 2H), 4.03 (q, J=7.1 Hz, 2 H), 4.85 (s, 1 H), 6.41 (s, 1 H), 7.25 (s, 1 H).

1. customquenched with 5% solution of sodium thiosulfate (30 mL)
2. stirringThe biphasic mixture was stirred for 30 mins
3. customthe layers were separated
4. washThe organic layer was washed with 1 N HCl, brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated to a red oil
7. customPurification by flash column chromatography (0% to 15% EtOAc in hexanes)

ORD record

ord-e34cf4c2b5a34e4ca61bf0dca3092c1b

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2