Hydrogen chloride-ethyl acetate → 1098106-78-5

HRID 341587Notes

Reaction equation

HRID 341587 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([CH3:20])([CH3:19])[CH2:10][NH:11]C(=O)OC(C)(C)C)[CH:5]=[CH:6][CH:7]=1.[ClH:21].CCOC(C)=O>CCOC(C)=O>[ClH:21].[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([CH3:20])([CH3:19])[CH2:10][NH2:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57608347HCID 57608347, compound

Product 1

HCID 666286841098106-78-5

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-(3-bromophenyl)-2,2-dimethylpropylcarbamate (29) (3.2 g, 9.35 mmol) was dissolved in EtOAc (55 mL), and a solution of HCl-EtOAc (˜4.2 M, 20 mL, 84 mmol) was added. The reaction was vented with a needle and stirred at room temperature for 2.5 h. The reaction was then diluted with hexanes and the white solid was collected on a flitted glass funnel. The mother liquor was concentrated under reduced pressure, suspended in ˜5-10% EtOAc-hexanes, and the white solid was collected and combined with the first batch. The solid was dried in a vacuum oven at room temperature overnight to give pure 3-(3-bromophenyl)-2,2-dimethylpropan-1-amine hydrochloride as a white solid. Yield (1.52 g): 1H NMR (400 MHz, CDCl3) δ 8.53 (br s, 2H), 7.37 (dq, J=1.2 and 8.0 Hz, 1H), 7.31 (t, J=1.6 Hz, 1H), 7.13 (t, J=7.7 Hz, 1H), 7.08 (dt, J=8.0, 1.6 Hz, 1H), 2.83-2.84 (m, 2H), 2.67 (s, 2H), 1.09 (s, 6H).

Workup

  1. customthe white solid was collected on a flitted glass funnel
  2. concentrationThe mother liquor was concentrated under reduced pressure
  3. customthe white solid was collected
  4. customThe solid was dried in a vacuum oven at room temperature overnight

Sources & evidence

ORD record
ord-440b73dca9ad428cb0c54c8ff6ba1ac6
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

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