Hydrochloric Acid → HCID 19094772, compound

HRID 1866834Notes

Reaction equation

HRID 1866834 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[C:16]([CH:17]2[CH2:19][CH2:18]2)=[CH:15][CH:14]=[CH:13][C:12]=1[Br:20])(=O)C.O.Cl>CO>[Br:20][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([CH:17]2[CH2:18][CH2:19]2)[C:11]=1[OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 69045518HCID 69045518, compound

Product 1

HCID 19094772HCID 19094772, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (276 mg, 2.00 mmol) was added to a solution of 2-bromo-6-cyclopropylphenyl acetate (316 mg, purity: 80%, 1.00 mmol) in methanol (2 ml), and the mixture was stirred at room temperature for 4 hours. After water (15 ml) and 4M hydrochloric acid (15 ml) were added to the reaction mixture, the mixture was extracted with ethyl acetate. The organic layer was combined, washed with a saturated aqueous NaCl solution, followed by drying with anhydrous sodium sulfate. After the solid was removed by filtration, the filtrate was concentrated to obtain a pale brown oil. This oil was purified by preparative thin layer chromatography (manufactured by Merck Co., Ltd, 1.05744, use of two sheets, development by hexane:ethyl acetate=30:1) to obtain 118 mg of 2-bromo-6-cyclopropylphenol.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with a saturated aqueous NaCl solution
  3. dry with materialby drying with anhydrous sodium sulfate
  4. customAfter the solid was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customto obtain a pale brown oil
  7. customThis oil was purified by preparative thin layer chromatography (manufactured by Merck Co., Ltd, 1.05744, use of two sheets, development by hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-fb3b1fe3ea1742df8bd4b61096efefa7
Source dataset
uspto-grants-2009_12
Patent number
US07629494B2

Reaction notes

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