Hydrochloric Acid → 4-(3-Bromobenzyloxy)-3,5-diiodo-benzoic Acid 3-bromobenzyl Ester

HRID 989411

반응식

HRID 989411 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([I:1])[C:10]([O:11][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=2)=[C:9]([I:12])[CH:8]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 12065Ioxynic acidHCID 699793-Bromobenzyl bromide

생성물 1

HCID 121488754-(3-Bromobenzyloxy)-3,5-diiodo-benzoic Acid 3-bromobenzyl Ester수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 3,5-diiodo-4-hydroxybenzoic acid (0.39 g, 1.0 mmol), 3-bromobenzyl bromide (0.62 g, 2.5 mmol), and cesium carbonate (0.98 g, 3.0 mmol) in 10 mL DMF was stirred for 15 hours at room temperature. The mixture was then poured into 1 M HCl (100 mL) and a white precipitate formed. The precipitate was isolated by vacuum filtration and was recrystallized from hot isopropanol/chloroform, yielding the title compound as bright white crystals (610 mg, 84%); 1H NMR (CDCl3) δ 8.48 (s, 2H), 7.80 (br. s, 1H), 7.58-7.49 (m, 4H), 7.38-7.28 (m, 3H), 5.31 (s, 2H), 5.01 (s, 2H).

후처리

  1. customa white precipitate formed
  2. customThe precipitate was isolated by vacuum filtration
  3. customwas recrystallized from hot isopropanol/chloroform

출처 및 근거

ORD 기록
ord-9fe9c7e04bdd46bdb323e1cb45c9fdca
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06638977B1

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