4-Fluorobenzoyl chloride → HCID 11279000, compound

HRID 993325Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][S:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1.[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>C1COCC1>[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](=[O:31])[CH:19]([C:16]2[CH:15]=[CH:14][C:13]([S:12][CH3:11])=[CH:18][CH:17]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: -78 °C

Procedure

1 N Lithium bis(trimethylsilyl)amide (25 mL, 25 mmol) was added dropwise to a solution of ethyl 2-(4-(methylthio)phenyl)acetate (5.05 g, 24 mmol), prepared according to the method of Example 73A, in THF (20 mL) maintained at −78° C. After 15 minutes the mixture was treated dropwise with a solution of 4-fluorobenzoyl chloride (2.85 mL, 24 mmol) in THF (50 mL), and the resulting mixture was stirred at −78° C. for 90 minutes. The mixture was quenched with saturated NH4Cl and extracted with ethyl acetate. The acetate layer was washed with water, brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was triturated with hexanes:ether, 15:1, to provide the desired product (yield: 7.25 g; 90%). MS (DCI-NH3) m/z 333 (M+H)+, 350 (M+NH4)+; 1H NMR (300 MHz, DMSO) δ1.18 (m, 3H), 2.45 (s, 3H), 4.15 (m, 2H), 6.15 (s, 1H), 7.23 (m, 2H), 7.35 (m, 4H), 7.85 (d, J=9 Hz, 2H).

Workup

customprepared
customThe mixture was quenched with saturated NH4Cl
extractionextracted with ethyl acetate
washThe acetate layer was washed with water, brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo
customThe residue was triturated with hexanes

Sources & evidence

ORD record: ord-59a03ddec7a9472fa20f9c1fd28e66d5
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472416B1

Reaction notes

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