Hydrochloric Acid → 3'-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid

HRID 2372255Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])C.Br[O-].[Na+].S(=O)(O)[O-:23].[Na+].Cl>O1CCOCC1>[F:18][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:23])=[CH:5][CH:6]=2)[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of 50 g (0.20 mol) of the above 4-acetyl 3'-fluoro-4'-methoxy biphenyl in 2 l of dioxane was added 1000 ml of an aqueous solution of sodium hypobromite (prepared from 338 g of sodium hydroxide and 486 g of bromine) over about 4 hours while cooling to not higher than 10° C., which was stirred at 25°-30° C. for about 3 hours. Thereafter, an aqueous saturated solution of sodium bisulfite was added to decompose the excessive amount of sodium hypobromite and then added with a concentrated hydrochloric acid to adjust pH to approximately 1. After the leaving over two nights, the precipitated crystal was filtered and recrystallized with ethanol and further with acetic acid to obtain 43 g (yield: 85%) of 3'-fluoro-4'-methoxybiphenyl-4-carboxylic acid.

Workup

waitAfter the leaving over two nights
filtrationthe precipitated crystal was filtered
customrecrystallized with ethanol and further with acetic acid

Sources & evidence

ORD record: ord-e6a26cd1d2a7449698f6cf042d81b8b7
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098602

Reaction notes

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