Water → (1,1'-Biphenyl)-4-carboxylic acid

HRID 404966Notes

Reaction equation

HRID 404966 reaction equation
[Li+].[I-].Cl[C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](COC3C=CC4C(=O)N(C5CCCC5)SC=4C=3)[CH:15]=2)[CH:7]=[CH:8][C:9]=1[C:10]([O:12]C)=[O:11].O>N1C=CC=CC=1>[C:6]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:4][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 66321Lithium iodideHCID 66799479Methyl 3-chloro-3'-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylate

Product 1

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidYield 110.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

LiI (0.042 g, 0.32 mmol) was added to a solution of methyl 3-chloro-3′-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylate (0.158 g, 0.32 mmol) in pyridine (5 mL). The reaction mixture was refluxed for 12 h, and then cooled to room temperature. Excess solvent was removed under vacuum. The product was purified by HPLC using isopropanol:water as the solvent system to afford 3-chloro-3′-(2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylic acid as a colorless solid (70 mg, 46% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.82 (d, 1H, J=8.5 Hz), 7.80 (d, 1H, J=8.6 Hz), 7.71-7.76 (m, 4H), 7.49-7.47 (m, 2H), 7.05 (d, 1H, J=8.5 Hz), 5.23 (s, 2H), 4.83-4.81 (m, 1H), 2.02-1.99 (m, 21-1), 1.62-1.60 (m, 6H). LC-MS (ESI) Calcd for C26H22ClNO4S [M+H]+: 480.09. Found: 479.95. HRMS (ESI) calcd for C26H22ClNO4S [M+H]+: 480.1031. Found: 480.1031.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. customExcess solvent was removed under vacuum
  3. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-85c3cd7546e3435b9cd2d5011ffe1653
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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