Hydrogen Peroxide → HCID 59849208, compound

HRID 604273Notes

Reaction equation

B1C2CCCC1CCC2.[CH3:10][O:11][C:12](=[O:26])[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15]([F:22])[C:14]=1[CH2:23][CH:24]=[CH2:25].[OH-:27].[Na+].OO>C1COCC1>[CH3:10][O:11][C:12](=[O:26])[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15]([F:22])[C:14]=1[CH2:23][CH2:24][CH2:25][OH:27]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 2 L, three necked, round-bottomed flask were charged 892 mL (0.45 mol) of 9-BBN (0.5M) and 100 mL of THF. After cooling to 0° C., 71 g (0.3 mol) of 2-allyl-3-fluoro-6-nitrobenzoic acid methyl ester in 150 mL of THF was added over 30 minutes and the mixture was stirred at room temperature for 5 hours. After cooling to 0° C., 700 mL of 1M NaOH aq was added into the reaction mixture, which was stirred for 30 minutes. To the mixture, 200 mL of hydrogen peroxide (35%) was added over 30 minutes then stirred at room temperature for 1 hours. The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water, a solution of sodium thiosulfate and brine, and was dried over sodium sulfate. The solvent was removed under reduced pressure to give 104 g of 3-fluoro-2-(3-hydroxy-propyl)-6-nitro-benzoic acid methyl ester as orange oil. The crude product was used for the next reaction.

Workup

temperatureAfter cooling to 0° C.
stirringwas stirred for 30 minutes
stirringthen stirred at room temperature for 1 hours
extractionThe mixture was extracted twice with ethyl acetate
washThe combined organic layers were washed with water
dry with materiala solution of sodium thiosulfate and brine, and was dried over sodium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-93013ad3296b469d8cc3b7efc6710376
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910585B2

Reaction notes

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