Cesium carbonate → HCID 57449661, compound

HRID 29686Notes

Reaction equation

HRID 29686 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 57449661HCID 57449661, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-53ef6fd9f7e04227913d0265f2724142
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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