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Potassium Carbonate → 1-(4-benzyloxy-2-nitrophenoxy)-2(2,3-Difluoro-6-nitrophenoxy) ethane

HRID 440129
Notes
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Reaction equation

HRID 440129 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][C:24]=1[N+:37]([O-:39])=[O:38]>CN(C=O)C.CCOCC>[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][O:12][C:3]2[C:4]([N+:9]([O-:11])=[O:10])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])=[C:24]([N+:37]([O-:39])=[O:38])[CH:25]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27337452,3-Difluoro-6-nitrophenolHCID 224091591-Bromo-2-(4-benzyloxy-2-nitrophenoxy)ethane

Product 1

HCID 571396561-(4-benzyloxy-2-nitrophenoxy)-2(2,3-Difluoro-6-nitrophenoxy) ethaneYield 69.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2,3-Difluoro-6-nitrophenol (0.7 g, 3.7 mmol) was stirred with K2CO3 (0.5 g, 3.7 mmol) in DMF (10 mL) for 10 min. Bromoethane 6 (1.1 g, 3.1 mmol) was added to the reaction mixture and heated at 70° C. for 24 hrs. The reaction mixture was diluted with ether (30 mL) and washed with water (20 mL) and then brine (20 mL). The ether layer was dried (MgSO4) and concentrated under reduced pressure. Fractionation of the crude product by flash chromatography with 4:1 hexane/ethyl acetate provided 7 as a yellow oil (960 mg, 63%). 1H NMR: 4.45 (t, J=5 Hz, 2H), 4.71 (t, J=5 Hz, 2H), 5.05 (s, 2H), 7.0-7.7 (m, 10H)

Workup

  1. washwashed with water (20 mL)
  2. dry with materialThe ether layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74ad91ec960d4992b1caafb0478ae4ed
Source dataset
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05516911

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes