Carbon Dioxide → 7-(Methylsulfanyl)-2-naphthoic acid

HRID 2238429Notes

Reaction equation

HRID 2238429 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([S:12][CH3:13])=[CH:7][CH:8]=2)[CH:3]=1.[Li]CCCC.[C:19](=[O:21])=[O:20]>C1COCC1>[CH3:13][S:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([C:19]([OH:21])=[O:20])=[CH:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 445509852-Bromo-7-(methylsulfanyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 445509867-(Methylsulfanyl)-2-naphthoic acidYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A stirred solution of 199 (850 mg, 3.36 mmol) in THF (10 mL) was treated at −78° C. with n-BuLi (2.5 M in hexanes, 1.48 mL, 3.70 mmol) under N2. The mixture was stirred at −78° C. for 15 nm in, then treated with excess CO2(g) and allowed to warm to room temperature. The solvent was removed under reduced pressure, and the residue was partitioned between water and EtOAc. The aqueous layer was acidified, and the resulting solid was crystallised from MeOH to give 7-(methylsulfanyl)-2-naphthoic acid (200) (577 mg, 79%): mp 217° C.; 1H NMR [(CD3)2SO] δ 13.0 (v br, 1H), 8.53 (d, J=0.7 Hz, 1H), 7.98-7.87 (m, 4H), 7.53 (dd, J=8.7, 1.9 Hz, 1H), 2.60 (s, 3H). Anal. (C12H10O2S) C, H.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between water and EtOAc
  4. customthe resulting solid was crystallised from MeOH

Sources & evidence

ORD record
ord-42b668baebf54e05b98cef3999cb7c98
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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