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Methanol → 1-Chloro-5-fluoro-2-methoxy-4-nitrobenzene

HRID 51444
Notes
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Reaction equation

HRID 51444 reaction equation
C(=O)([O-])OCC[C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([F:14])=[CH:7][C:6]=1[Cl:15].[C:18](=O)([O-])[O-:19].[Cs+].[Cs+].IC.CO>CN(C)C=O.O>[Cl:15][C:6]1[CH:7]=[C:8]([F:14])[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[O:19][CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66588385(2-Chloro-4-fluoro-5-nitrophenyl)-ethyl carbonate

Product 1

HCID 27792951-Chloro-5-fluoro-2-methoxy-4-nitrobenzeneYield 97.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

A solution of 15.0 g of (2-chloro-4-fluoro-5-nitrophenyl)-ethyl carbonate in 100 ml of dimethyl formamide was treated with 18.6 g of cesium carbonate, 7.1 ml of iodomethane and 7 ml of methanol and stirred overnight at room temperature. The reaction mixture was poured into water and extracted twice with ether. The extracts were washed twice with water and then with brine, dried over magnesium sulfate and concentrated to afford 11.4 g of the subtitle compound. mp. 69-70° C. Ex. 57, C.

Workup

  1. extractionextracted twice with ether
  2. washThe extracts were washed twice with water
  3. dry with materialwith brine, dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-faa14b06cf2b4e0d9eae0409f8197195
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713645B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes