Sodium Iodide → HCID 68500397, compound

To a suspension of 4-hydroxybenzophenone (4.0 g, 19.8 mmol) in CH3CN (30 mL) was added K2CO3 (8.20 g, 59.3 mmol). The mixture was refluxed under nitrogen for 1 h. Cooled to room temperature, 2-(2-chloroethoxy)ethanol (4.3 mL, 39.6 mmol) was added, followed by addition of NaI (3.00 g, 19.8 mmol). The reaction mixture was refluxed under nitrogen overnight. The mixture was cooled to room temperature and EtOAc (50 mL) was added. The precipitated white solid was filtered and washed with EtOAc (50 mL). The filtrate was transferred to a separatory funnel and washed with 1 N NaOH, water, brine and dried over Na2SO4. Concentration yielded a yellow oil which was further purified by chromatography on a silica gel column eluted with a gradient from hexanes to 70% EtOAc:hexanes to give 7 as colorless crystals (4.96 g, 88%). mp 31-32° C. 1H NMR (400 MHz, CDCl3): δ 3.65-3.75 (m, 2H), 3.75-3.80 (m, 2H), 3.90-3.95 (m, 2H), 4.20-4.25 (m, 2H), 6.99 (d, J=8.8 Hz, 2H), 7.45-7.50 (m, 2H), 7.55-7.60 (m, 1H), 7.70-7.80 (m, 2H), 7.83 (d, J=8.8 Hz, 2H). LRMS (ESI): m/z 287 (M+H)+.

1. temperatureThe mixture was refluxed under nitrogen for 1 h
2. temperatureThe reaction mixture was refluxed under nitrogen overnight
3. temperatureThe mixture was cooled to room temperature
4. filtrationThe precipitated white solid was filtered
5. washwashed with EtOAc (50 mL)
6. customThe filtrate was transferred to a separatory funnel
7. washwashed with 1 N NaOH, water, brine
8. dry with materialdried over Na2SO4
9. concentrationConcentration
10. customyielded a yellow oil which
11. customwas further purified by chromatography on a silica gel column
12. washeluted with a gradient from hexanes to 70% EtOAc

ORD record

ord-19bce0e52818439aa976f2ba4529e61c

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723393B2