Hydrochloric Acid → HCID 67421122, compound

HRID 1423908Notes

Reaction equation

HRID 1423908 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Li+].[OH-].Cl>CO.C1COCC1.O>[F:10][C:8]1[CH:7]=[CH:6][C:5]([S:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH:9]=1)[C:3]([OH:31])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67419398HCID 67419398, compound

Product 1

HCID 67421122HCID 67421122, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 5-fluoro-2-tritylsulfanyl-benzoic acid methyl ester (4.74 g, 11.2 mmol) and LiOH (1.74 g, 41.4 mmol) in 80 mL of MeOH/THF/H2O (1/2/1) was stirred at rt overnight. The reaction mixture was acidified to pH 4 using 1 N HCl. The precipitate was collected by filtration, rinsed with water and dried in vacuo to provide 5-fluoro-2-tritylsulfanyl-benzoic acid (4.16 g). MS ESI(+) m/e: 415.13 (M+1).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washrinsed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-518859145bb14c88b9578bcdfdb1cfad
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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