Water → Tert-butyl 4-chloro-3-nitrobenzoate

HRID 1274129Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14]([OH:18])([CH3:17])([CH3:16])[CH3:15].N1C=CC=CC=1.O>C(Cl)Cl>[C:14]([O:18][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4-chloro-3-nitrobenzoylchloride (8.80 g, 40 mmol) in CH2Cl2 (20 mL) was added to a solution of tert-butyl alcohol (7.6 mL, 80 mmole) and pyridine (6.6 mL, 80 mmole) at 25° C. The mixture was stirred at 25° C. for 12 h then H2O (30 mL) was added. The aqueous solution was extracted with ethyl ether (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give a yellowish solid residue. Purification of the residue by flash column chromatography (gradient elution 0 to 15% EtOAc/hexanes) provided the title compound (8.11 g, 79%): TLC (Rf =0.50; 15% EtOAc/hexanes); 1H NMR (CDCl3) δ 8.41 (s, 1H), 8.13 (d, 1H, J=8.0), 7.63 (d, 1H, J=8.3), 1.63 (s, 9H); 13C NMR (CDCl3)δ 162.4, 147.6, 133.2, 131.6, 130.5, 126.0, 124.4, 82.6, 27.8; Anal. (C11H12N1O4Cl) C, H, N.

Workup

extractionThe aqueous solution was extracted with ethyl ether (3×100 mL)
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give a yellowish solid residue
customPurification of the residue
washby flash column chromatography (gradient elution 0 to 15% EtOAc/hexanes)

Sources & evidence

ORD record: ord-8ccfb71b119f415f95c744ffc5c59f0a
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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