Chloromethyl Methyl Ether → HCID 86674221, compound

HRID 1425604Notes

Reaction equation

HRID 1425604 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.Cl[CH2:28][O:29][CH3:30]>C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:28][O:29][CH3:30])=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 136352338HCID 136352338, compound

Product 1

HCID 86674221HCID 86674221, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(5-bromo-3-nitropyridin-2-yl)phenol (280 mg, 0.95 mmol) and DIPEA (360 mmg, 2.85 mmol) in 5 mL of dry DCM at 0° C. was added dropwise chloro(methoxy)methane (210 mg, 1.9 mmol). The reaction was warmed to rt and stifling was continued for 3 h and the diluted with EtOAc (30 mL), washed with water (3×30 mL) and dried over MgSO4. Solvent was removed under reduced pressure and the residue was purified by silica chromatography (EtOAc in hexane, 5% to 35%) to afford 5-bromo-2-(4-(methoxymethoxy)phenyl)-3-nitropyridine as a yellow wax (260 mg, 80%). MS (ESI) m/z [M+H]+339, 341.

Workup

  1. washwashed with water (3×30 mL)
  2. dry with materialdried over MgSO4
  3. customSolvent was removed under reduced pressure
  4. customthe residue was purified by silica chromatography (EtOAc in hexane, 5% to 35%)

Sources & evidence

ORD record
ord-317d5defeb904be3b223008fa46d2f34
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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