2-Bromo-1-isopropoxy-3-nitrobenzene → HCID 18687703, compound

HRID 1872870Notes

Reaction equation

HRID 1872870 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[C:9]([SH:15])=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.Br[C:17]1[C:22]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:21][CH:20]=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]>CN(C=O)C>[F:7][C:8]1[C:9]([S:15][C:19]2[CH:20]=[CH:21][C:22]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:17][C:18]=2[N+:27]([O-:29])=[O:28])=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.[F:7][C:8]1[C:9]2[S:15][C:19]3[C:20](=[CH:21][C:22]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:17][CH:18]=3)[O:14][C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 186877232-Bromo-1-isopropoxy-3-nitrobenzeneHCID 18687756205187-70-8HCID 23665647Potassium tert-butoxide

Product 2

HCID 18687703HCID 18687703, compoundYield 45%HCID 18687743HCID 18687743, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium tert-butoxide (360 mg, 3.2 mmol) was added to a stirred, degassed, solution of 3-fluoro-2-mercaptophenol (390 mg, 2.7 mmol) and 2-bromo-3-isopropoxy-nitrobenzene in 20 mL anhydrous DMF and the resulting burgandy-colored reaction heated at 80° C. under N2 overnight (17 h). After cooling to room temperature 10% aqueous HCL (100 ml) was added and the reaction mixture washed with EtOAc (2×75 ml). The combined organics were rinsed with water (2×200 ml), and brine (200 ml), dried (Na2SO4), and concentrated in vacuo to a viscous orange-brown oil. Purification by column chromatography afforded 390 mg (45% from O-2-(4-methoxybenzyl)thio-3-fluorophenyl N,N-diethylcarbamate) of 3-fluoro-2-((4-isopropoxy-2-nitrophenyl)thio)phenol as a yellow solid along with 60 mg (8%) of 1-fluoro-7-isopropoxyphenoxathiin.

Workup

  1. customdegassed
  2. temperatureAfter cooling to room temperature 10% aqueous HCL (100 ml)
  3. additionwas added
  4. washthe reaction mixture washed with EtOAc (2×75 ml)
  5. washThe combined organics were rinsed with water (2×200 ml), and brine (200 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo to a viscous orange-brown oil
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-519dbe19499e47a5a78517136d38b787
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

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