Carbon Dioxide → 2-(tert-Butoxycarbonyl)-6-chloro-4-trifluoromethylbenzoic acid

HRID 3129

Reaction equation

C(OC(N[C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([Cl:19])[CH:10]=1)=O)(C)(C)C.[C:20]([Li])([CH3:23])([CH3:22])[CH3:21].[C:25](=[O:27])=[O:26].[OH2:28].[O:29]1[CH2:33]CCC1>CCCCC>[C:20]([O:26][C:25]([C:9]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:11]([Cl:19])[C:10]=1[C:33]([OH:29])=[O:28])=[O:27])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: -75 °C

Procedure

To a cold (-100° C.) stirred solution of N-(tert-butoxycarbonyl)-3-chloro-5-trifluoromethylaniline 93.4 g, 11.5 mM) in dry tetrahydrofuran (30 mL) under a nitrogen atmosphere was added dropwise t-butyllithium (14.2 mL of 1.7 M solution, 24.2 mM) in pentane. The temperature of the reaction mixture was maintained at -103° to -98° C. during the addition and for 3.25 hr after the addition was completed. Crushed Dry Ice was then added to the cold reaction mixture which, after being allowed to warm to -75° C., was poured into water. The resulting mixture was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated to leave (3.2 g, 82%) the title compound as a solid white foam.

Workup

temperatureThe temperature of the reaction mixture was maintained at -103° to -98° C. during the addition and for 3.25 hr
additionafter the addition
extractionThe resulting mixture was extracted with ethyl acetate
dry with materialthe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1eb43454a5ef481dbf4ca95331913c1b
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733910

Linked notes

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