Tetrahydrofuran → HCID 90310642, compound

HRID 1519144Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][CH3:10].[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1.C([Mg]Cl)(C)C.C1(=O)CCC1>CCOCC>[F:8][C:4]1[C:3]([O:9][CH3:10])=[C:2]([C:15]2([OH:14])[CH2:11][CH2:12][CH2:13]2)[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 500 mL round-bottomed flask were added a stir bar, 2-bromo-6-fluoroanisol (11.03 g, 53.8 mmol) and dry THF (215 mL). The flask was purged with nitrogen and cooled to 0° Celsius before adding 2.0 M i-PrMgCl in THF (60 mL, 120 mmol) over the course of 3 min. The resultant mixture was stirred for 2 h before adding cyclobutanone (5.0 mL, 67 mmol). The resultant mixture was stirred for 0.5 hour before diluting with Et2O (500 mL) and washing with saturated NH4Cl followed by brine. The organic layer was isolated, dried over MgSO4, filtered and concentrated to dryness to give a pale-yellow oil. Subjecting the residue to FCC yielded 1-(3-fluoro-2-methoxyphenyl)cyclobutanol as a pale-yellow oil (5.18 g, 49%). 1H NMR (600 MHz, CDCl3) δ 7.07-7.03 (m, 1H), 7.03-6.98 (m, 1H), 6.98-6.94 (m, 1H), 3.99 (d, J=2.4, 3H), 3.39 (s, 1H), 2.57-2.45 (m, 2H), 2.41-2.31 (m, 2H), 2.17-2.05 (m, 1H), 1.75-1.65 (m, 1H).

Workup

additionTo a 500 mL round-bottomed flask were added a stir bar
customThe flask was purged with nitrogen
washwashing with saturated NH4Cl
customThe organic layer was isolated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness
customto give a pale-yellow oil

Sources & evidence

ORD record: ord-98fbb9bc59fa4994bdae5157290fee2f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073876B2

Reaction notes

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