Potassium Carbonate → HCID 70816329, compound

HRID 1842942Notes

Reaction equation

HRID 1842942 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[F:18].C[O:20][CH:21](O)[CH3:22]>O>[F:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[CH2:8][O:20][CH2:21][CH2:22][O:4][CH3:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30156371-MethoxyethanolHCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzene

Product 1

HCID 70816329HCID 70816329, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of K2CO3 (8.8 g, 64.0 mmol, 1.5 eq) in methoxyethanol (100 mL) was added 1-(bromomethyl)-2-fluoro-4-nitrobenzene (10.0 g, 42.0 mmol, 1 eq) and the mixture was stirred at RT for 5 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (30 mL×2). The ethyl acetate layers were collected and dried (Na2SO4) and evaporated under vacuum. The residue was purified by CC using PE/EtOAc (17:3) as eluant to get 2-fluoro-1-((2-methoxyethoxy)methyl)-4-nitrobenzene (4 g, 40%) as oil (TLC system: PE/EtOAc (7:3), Rf: 0.5).

Workup

  1. extractionextracted with EtOAc (30 mL×2)
  2. customThe ethyl acetate layers were collected
  3. dry with materialdried (Na2SO4)
  4. customevaporated under vacuum
  5. customThe residue was purified by CC

Sources & evidence

ORD record
ord-5d889300f9694f7fa157e4bf2fd55da1
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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