Dimethyl Sulfoxide → HCID 89647839, compound

HRID 929448Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[C:12]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)([CH2:15][CH3:16])([CH3:14])[CH3:13].CS(C)=O>>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]([CH2:15][CH3:16])([CH3:13])[CH3:14])=[CH:18][CH:19]=1

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 66434-tert-Pentylphenol

HCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 89647839HCID 89647839, compoundYield 99%

Procedure

Following procedure A, 3,4-difluoronitrobenzene (502 mg, 3.16 mmol, 1.00 eq) and 4-tert-pentylphenol (693 mg, 4.22 mmol, 1.34 eq) were dissolved in DMSO (6 mL) Anhydrous K2CO3 (656 mg, 4.75 mmol, 1.50 eq) was added and the reaction mixture was stirred at room temperature for 22 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:50) to afford the title compound as pale yellow oil (943 mg, 3.11 mmol, 99% yield). Rf=0.61 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C17H19NO3+ [M+H]+ 304.1343. found: 304.1332. 1H NMR (400 MHz, CDCl3) δ 8.08 (dd, J=10.3, 2.7 Hz, 1H, aromatic H), 7.96 (ddd, J=9.1, 2.7, 1.5 Hz, 1H, aromatic H), 7.42-7.35 (m, 2H, aromatic H), 7.07-6.99 (m, 2H, aromatic H), 6.95 (dd, J=9.1, 8.0 Hz, 1H, aromatic H), 1.66 (q, J=7.4 Hz, 2H, Ar—C(CH3)2CH2CH3), 1.31 (s, 6H, Ar—C(CH3)2CH2CH3), 0.71 (t, J=7.4 Hz, 3H, Ar—C(CH3)2CH2CH3). 13C NMR (101 MHz, CDCl3) δ 153.40, 152.19, 151.98, 151.87, 150.88, 147.11, 127.97, 120.71, 120.68, 119.34, 117.73, 117.71, 113.11, 37.92, 37.08, 28.64.

Workup

additionwas added
extractionAfter extraction with Et2O
customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:50)

Sources & evidence

ORD record: ord-d65e6e3f9eac4d0bb58c4e90d9cd6ca9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296682B2

Reaction notes

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