Cesium carbonate → methyl 2-bromo-4-[[(E)-(4-tert-butylphenyl)methylideneamino]oxymethyl]benzoate

HRID 29686노트

반응식

HRID 29686 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[Br:12].[C:14]([C:18]1[CH:26]=[CH:25][C:21]([CH:22]=[N:23][OH:24])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:24]/[N:23]=[CH:22]/[C:21]2[CH:25]=[CH:26][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=2)=[CH:6][C:5]=1[Br:12]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 1275951N-[(4-tert-butylphenyl)methylidene]hydroxylamineHCID 19806367Methyl 2-bromo-4-(bromomethyl)benzoate

생성물 1

HCID 57449661methyl 2-bromo-4-[[(E)-(4-tert-butylphenyl)methylideneamino]oxymethyl]benzoate수율 83%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

This compound was produced using similar methods as those used in Step 5, example 27, starting with 2-bromo-4-bromomethyl-benzoic acid methyl ester (0.40 g, 1.30 mmol), 4-tert-butyl-benzaldehyde oxime (0.24 g, 1.36 mmol) and cesium carbonate (1.69 g, 5.20 mmol) in acetone (50 mL). The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 6/94) to give 2-bromo-4-[({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)methyl]benzoic acid methyl ester (0.43 g, 83%) as a clear, colorless oil. 1H NMR (400 MHz, CDCl3); δ 8.13 (s, 1H), 7.78 (d, 1H), 7.69 (s, 1H), 7.49 (d, 2H), 7.39-7.36 (m, 3H), 5.18 (s, 2H), 3.92 (s, 3H), 1.32 (s, 9H).

후처리

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

출처 및 근거

ORD 기록
ord-53ef6fd9f7e04227913d0265f2724142
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

반응 노트

불러오는 중…