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

HRID 1839907ノート

反応式

HRID 1839907 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4526f125098a44d7b5f83e81d766ddb3
出典データセット
uspto-grants-2004_01
特許番号
US06677473B1

反応ノート

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