tert-Butanol → 5-iodo-2-methylbenzoic Acid t-butyl Ester

HRID 1767248Notes

Reaction equation

HRID 1767248 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl.CN(C)CCCN=C=NCC.[C:24](O)([CH3:27])([CH3:26])[CH3:25]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[C:24]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=1[CH3:11])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 6386tert-ButanolHCID 6217455-Iodo-2-methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 695076315-iodo-2-methylbenzoic Acid t-butyl EsterYield 65%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-iodo-2-methylbenzoic acid (760 mg, 2.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (670 mg, 3.5 mmol), 4-dimethylaminopyridine (425 mg, 3.5 mmol), and t-butanol (1.07 g, 14.5 mmol) in dichloromethane (10 ml) was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (25 ml) and washed with 5% NaHCO3, 1M HCl, water and, brine. The organic phase was dried and evaporated to give a pale yellow solid 600 mg 65%.

Workup

  1. washwashed with 5% NaHCO3, 1M HCl, water and, brine
  2. customThe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-ccc9dd58475743b58016bb06b7e85964
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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