Carbon Dioxide → HCID 59473815, compound

HRID 2069835Notes

Reaction equation

C([Mg]Cl)(C)C.[Li]CCCC.Br[C:12]1[C:17]([CH3:18])=[CH:16][C:15]([N:19]([CH3:21])[CH3:20])=[CH:14][C:13]=1[F:22].[C:23](=[O:25])=[O:24].[OH-].[Na+]>C1COCC1>[CH3:20][N:19]([CH3:21])[C:15]1[CH:16]=[C:17]([CH3:18])[C:12]([C:23]([OH:25])=[O:24])=[C:13]([F:22])[CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

At 0° C., to a solution of iPrMgCl (9.10 mL, 2.0M THF, 1.2 eq.) in THF (14 mL) was added nBuLi (22.3 mL, 1.6 M Hexanes, 2.4 eq.). After 10 min., now yellow, homogeneous solution was cooled to −78° C., and to this was added a solution of (4-Bromo-3-fluoro-5-methyl-phenyl)-dimethyl-amine (3.52 g, 15.2 mmol) in THF (18 mL). Following the disappearance of the yellow color, the TLC after 20 min. showed no starting material. CO2(g) was canula transferred into the reaction mixture, which was warmed to room temperature, after 20 min., and added to 1N NaOH. The aqueous layer was acidified with 1NHCl(aq) and extracted with EtOAc. Organic extracts were dried (MgSO4), filtered, concentrated in vacuo to give a crude solid, which was purified by flash chromatography (SiO2, 40%-100% EtOAc/Hexanes) to give 4-Dimethylamino-2-fluoro-6-methyl-benzoic acid as a white solid (2.91 g, 97%).

Workup

waitthe TLC after 20 min. showed
temperaturewas warmed to room temperature, after 20 min.
extractionextracted with EtOAc
dry with materialOrganic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give a crude solid, which
customwas purified by flash chromatography (SiO2, 40%-100% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-0e42e7096c4f4c3e9334c945343c9ed5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299077B2

Reaction notes

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