Potassium Carbonate → 2-(Cyclopropylthio)-5-nitrobenzaldehyde

HRID 1515541Notes

Reaction equation

[CH:1]1([SH:4])[CH2:3][CH2:2]1.F[C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=1[CH:8]=[O:9].C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(OCC)C.CN(C=O)C.CCOC(C)=O>[CH:1]1([S:4][C:6]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=2[CH:8]=[O:9])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 45 °C

Procedure

Freshly prepared cyclopropyl thiol in THF/diethyl ether (J. Am. Chem. Soc. 1992, 114(9), 3497) was added to 2-fluoro-5-nitrobenzaldehyde (3.4 g, 20 mmol, 1.0 eq.) and K2CO3 (4.83 g, 35 mmol) in DMF (20 mL). The mixture was stirred at 45° C. for 1.0 h and at rt over night. It was diluted with EtOAc and washed with water. The aqueous was extracted with EtOAc and the combined organic layers were washed with brine and dried over Na2SO4. After evaporation of solvent, the crude was tritutated with EtOAc/hexanes (70/120). The solid was collected to give 76A (3.2 g). The filtrate was condensed and triturated again to give a second crop of 76A (0.5 g, total yield 85%). 1H NMR (400 MHz, CDCl3) δ ppm 0.74-0.83 (m, 2H) 1.20-1.28 (m, 2H) 2.13-2.19 (m, 1H) 7.95 (d, J=9.23 Hz, 1H) 8.33 (dd, J=8.79, 2.64 Hz, 1H) 8.62 (d, J=2.64 Hz, 1H) 10.15 (s, 1H).

Workup

washwashed with water
extractionThe aqueous was extracted with EtOAc
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
customAfter evaporation of solvent
customThe solid was collected

Sources & evidence

ORD record: ord-e0c576c4924f403484ed1338e3426851
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222453B2

Reaction notes

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