Chloroiodomethane → HCID 86703560, compound

HRID 1849689Notes

Reaction equation

[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([CH3:27])[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:2]1.Cl[CH2:29]I.C([Zn]CC)C>ClCCCl>[C:12]([O:11][C:9](=[O:10])[C:8]1[CH:16]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]([O:18][CH2:19][C:20]2([CH3:27])[CH2:25][CH2:24][C:23]3([CH2:29][CH2:26]3)[CH2:22][CH2:21]2)=[CH:6][C:7]=1[F:17])([CH3:14])([CH3:13])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((1-methyl-4-methylenecyclohexyl)methoxy)benzoate (0.30 g, 0.804 mmol) in 1,2-dichloroethane (2 mL), was added chloroiodomethane (0.21 mL, 2.65 mmol), followed by diethylzinc (1M solution in hexanes, 1.33 mL, 1.33 mmol). The reaction mixture was stirred at 0° C. for 2 hours and then quenched with 1N aqueous hydrochloric acid solution. The aqueous layer was separated and extracted with dichloromethane (3×30 mL). The combined organics were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography (0% to 5% ethyl acetate in hexanes) afforded the title compound (0.29 g, 93%) as a colorless oil: MS (ES+) m/z 333.2 (M−55).

Workup

customquenched with 1N aqueous hydrochloric acid solution
customThe aqueous layer was separated
extractionextracted with dichloromethane (3×30 mL)
dry with materialThe combined organics were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customPurification of the residue by column chromatography (0% to 5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-dc51366dd7f64bfc8a3c84dd527f5b63
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

Loading…