Hydrochloric Acid → 3-Iodo-4-methoxybenzoic acid

HRID 1511402노트

반응식

HRID 1511402 반응식
[OH-].[Li+].[I:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([O:9]C)=[O:8].Cl>C1COCC1.CO.O.O>[I:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([OH:9])=[O:8]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 316980Methyl 3-iodo-4-methoxybenzoate

생성물 1

HCID 6241583-Iodo-4-methoxybenzoic acid수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

Lithium hydroxide (72 mg, 1.71 mmol) was added to a mixture of methyl 3-iodo-4-methoxybenzoate (100 mg, 0.342 mmol) in 3.0 mL of a 3:1:1 THF-MeOH-water solution at room temperature. The mixture was stirred for eight hours in the dark and than diluted with H2O (2 mL). The solution was acidified to pH=2 by the dropwise addition of concentrated HCl. The solution was extracted twice with EtOAc (10 mL portions) and the combined organic layers dried (Na2SO4), filtered, and concentrated to afford acid 26 (95 mg, 100%) as a yellow solid that was suitable for use without further purification: 1H NMR (400 MHz, DMSO) δ 8.24 (d, J=2.0 Hz, 1H), 7.92 (dd, J=2.0, 8.7 Hz, 1H), 7.07 (d, J=8.7 Hz, 1H), 3.88 (s, 3H).

후처리

  1. extractionThe solution was extracted twice with EtOAc (10 mL portions)
  2. dry with materialthe combined organic layers dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0ad80adbcf664836a1db89fdc2e8eb02
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212012B2

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