Hydrochloric Acid → (4-Benzoyl-2,6-diiodophenoxy)-acetic Acid Benzyl Ester

HRID 1839907노트

반응식

HRID 1839907 반응식
[OH:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[I:17].Br[CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:1][C:2]1[C:3]([I:17])=[CH:4][C:5]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:7]=1[I:8])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 9911585(4-Hydroxy-3,5-diiodo-phenyl)-phenyl-methanone

생성물 1

HCID 9873430(4-Benzoyl-2,6-diiodophenoxy)-acetic Acid Benzyl Ester수율 38%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (4-hydroxy-3,5-diiodophenyl)-phenyl-methanone (as prepared in Example 6, 2.25 g, 5.0 mmol) and benzyl 2-bromoacetate (1.71 g, 7.5 mmol) in 50 mL DMF was added cesium carbonate (4.1 g, 13 mmol). The resulting suspension was stirred for 15 hours, then the reaction mixture was poured into ˜150 mL 1 M HCl. A pale oil formed, and the supernatant was removed by decantation. The oil was crystallized from hot isopropanol, yielding the title compound as colorless crystals (1.13 g, 38%). 1H NMR (400 MHz, CDCl3): δ 8.18 (s, 2H), 7.77-7.74 (m, 2H), 7.63 (tt, J=7.4, 1.2 Hz, 1H), 7.54-7.50 (m, 2 H), 7.45-7.35 (m, 5H), 5.33 (s, 2H), 4.71 (s, 2H). TLC (4:1 Hex:EtOAc), Rf 0.52. LRMS (EI+) calc'd for [C22H16I2O4+H] 598.9, found 598.8.

후처리

  1. customA pale oil formed
  2. customthe supernatant was removed by decantation
  3. customThe oil was crystallized from hot isopropanol

출처 및 근거

ORD 기록
ord-4526f125098a44d7b5f83e81d766ddb3
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677473B1

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