Methanol → HCID 67173430, compound

HRID 1256097Notes

Reaction equation

HRID 1256097 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][C:12](OC)=[O:13].CO.O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 67172692HCID 67172692, compound

Product 1

HCID 67173430HCID 67173430, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(2-bromo-5-nitrophenyl)acetate (14 g, 51 mmol) in THF (150 mL) was cooled to 0° C., then MeOH (15 ml) was added slowly, followed by stirring at room temperature overnight. Water was added to terminate the reaction. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 2-(2-bromo-5-nitrophenyl)ethanol (12 g, yield 96%). 1H NMR: 400 MHz CDCl3 δ 8.18-8.17 (m, 1H), 8.18-8.17 (m, 1H), 7.96-7.93 (m, 1H), 7.74-7.72 (m, 1H), 3.97-3.94 (m, 2H), 3.13-3.10 (m, 2H).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b3cf2e0f93f4e05856cd78b9cfa01e5
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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