Hydrochloric Acid → 2-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid

HRID 29239Notes

Reaction equation

HRID 29239 reaction equation
C([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)=[CH:14][C:9]=2[O:8][C:7]=1[C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])=[O:5])C.[OH-].[K+].Cl>CO.O.C1COCC1>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[C:22]([C:7]1[O:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][C:10]=2[C:6]=1[C:4]([OH:5])=[O:3])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 597888932-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid ethyl ester

Product 1

HCID 597889522-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 2-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid ethyl ester from step 5 (91.3 mg, 0.20 mmol, 1 eq) in MeOH/H2O/THF (2 mL, ratio:1:1:1) solution was added potassium hydroxide (72.0 mg, 0.52 mmol, 2.6 eq). The reaction mixture was stirred at rt for 6 h. 2N HCl (500 uL) was added to the reaction mixture and the solvent was removed under reduced pressure. The residue was purified by pre-HPLC to afford an yellow solid (68 mg, 80%) as desired product. 1H-NMR (CDCl3): δ 8.58 (d, J=8.3 Hz, 1H), 7.75 (dd, J=1.5, 8.3 Hz, 1H), 7.69 (s, 1H), 7.57 (d, J=1.5 Hz, 1H), 7.56 (d, J=8.3 Hz, 1H), 7.46 (dd, J=1.5, 8.3 Hz, 1H), 7.43 (m, 2H), 7.34 (t, 1H), 7.21 (d, J=8.3 Hz, 1H), 2.43 (s, 3H); LC-MS (MH+=425/427).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-09e637ea5c6d41d299852bc0eb26d940
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Reaction notes

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