Sulfuric Acid → 3-[(3-Carboxyphenyl)sulfinyl]benzenecarboxylic acid

HRID 2055918Notes

Reaction equation

HRID 2055918 reaction equation
C([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)(O)=O.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.CC(O)[C:55]([O-:57])=[O:56].C1C=CC([Hg+])=CC=1.C(N(CCO)CCO)C[OH:68].OS([O-])=O.[Na+].OS(O)(=O)=O>N1C=CC=CC=1>[C:17]([C:13]1[CH:12]=[C:11]([S:10]([C:5]2[CH:4]=[C:9]([C:55]([OH:57])=[O:56])[CH:8]=[CH:7][CH:6]=2)=[O:68])[CH:16]=[CH:15][CH:14]=1)([OH:19])=[O:18]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 166410023-[(Carboxyphenyl)sulfanyl]benzenecarboxylic acidHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 23665763Sodium BisulfiteHCID 25199577Phenylmercuritriethanolammonium lactate

Product 1

HCID 42754373-[(3-Carboxyphenyl)sulfinyl]benzenecarboxylic acidYield 78.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred ice cooled solution of 3-[(carboxyphenyl)sulfanyl]benzenecarboxylic acid (GM71/7, VIB-006) (1.0 g, 3.65 mmol) in aqueous pyridine ((1/1) 5.84 mL), phenyl trimethylammonium tribromide (1.43 g, 3.8 mmol) was gradually added in portions to keep the temperature between 0 and 10° C. When addition was complete, the reaction mixture was stirred at room temperature for 24 hours. Then the unreacted PTAB was decomposed with 40% NaHSO3 (3.65 mL). Ice water (14.6 mL) was then added and the reaction mixture was acidified with 2N H2SO4. A solid precipitated to afford (833.0 mg, 78.7%) of the desired 3-[(3-Carboxyphenyl)sulfinyl]benzenecarboxylic acid (GM71/21, VIB-032) as a white powder. M.S. m/z 288.70 (M−1)+. 1H NMR (300.13, d6-DMSO) 7.67 (2H, t, 2×ArH, J=7.8 Hz), 7.99 (4H, m, 4×ArH), 8.23 (2H, m, 2×ArH). 1H NMR (300.13, d6-DMSO) 38.8, 132.2, 133.1, 133.4, 139.5. Found C, 53.97, H, 3.22%, C14H10O5S.1.0 H2O requires C, 54.49, H, 3.24%.

Workup

  1. customthe temperature between 0 and 10° C
  2. additionWhen addition
  3. customA solid precipitated

Sources & evidence

ORD record
ord-f2fe61ae6e194059abfa1d85df196ac6
Source dataset
uspto-grants-2008_02
Patent number
US07332631B2

Reaction notes

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