Sodium Hydroxide → (R)-4-bromo-alpha-methylbenzylamine

HRID 2193448Notes

Reaction equation

HRID 2193448 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10]C(=O)C(F)(F)F)[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57984669(R)-N-(1-(4-bromophenyl)ethyl)-2,2,2-trifluoroacetamide

Product 1

HCID 853000(R)-4-bromo-alpha-methylbenzylamineYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-N-(1-(4-bromophenyl)ethyl)-2,2,2-trifluoroacetamide (20 g, 68 mmol) was dissolved in methanol (200 mL) and cooled in an ice-water bath. Then aqueous NaOH (2 M, 100 mL) was added to the above mixture. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated and then partitioned between CH2Cl2 and water. The aqueous layer was extracted with addition CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered and concentrated to give (R)-1-(4-bromophenyl)ethan amine (9.8 g, 73%). 1H NMR (DMSO): 1.19 (m, 3H), 3.92 (m, 1H), 7.28 (m, 2H), 7.42 (m, 2H).

Workup

  1. temperaturecooled in an ice-water bath
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between CH2Cl2 and water
  4. extractionThe aqueous layer was extracted with addition CH2Cl2
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0c639325e36140f7a18139fff3c6f263
Source dataset
uspto-grants-2012_12
Patent number
US08329897B2

Reaction notes

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