Hydrochloric Acid → 2-(4-Bromophenoxy)-2-methyl-1-(pyrrolidin-1-yl)propan-1-one

HRID 646124Notes

Reaction equation

HRID 646124 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]([CH3:17])([CH3:16])[C:13](Cl)=[O:14])=[CH:9][CH:8]=1.Cl>CC#N.[Cl-].[Na+].O>[Br:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]([CH3:16])([CH3:17])[C:13]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 45923264HCID 45923264, compound

Product 1

HCID 686947812-(4-Bromophenoxy)-2-methyl-1-(pyrrolidin-1-yl)propan-1-oneYield 94.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Pyrrolidine (1.54 g, 21.6 mmol) in anhydrous MeCN (10 mL) was added with stirring to 2-(4-bromophenoxy)-2-methylpropanoyl chloride (2 g, 7.2 mmol) in anhydrous MeCN (10 mL) at 0° C. The mixture was stirred at room temperature for 18 h and acidified with HCl (aq. 1M, 40 mL). Brine was added and the mixture was extracted with CH2Cl2. The combined extracts were washed with NaHCO3 (aq. sat) and brine, dried (Na2SO4), and concentrated to give the sub-title compound (2.12 g, 94%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. washThe combined extracts were washed with NaHCO3 (aq. sat) and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1a2c603c73604cefa9e76b385285ffd3
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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