Sodium Hydroxide → 5-(4-Bromophenyl)-3,4-dihydro-2h-pyrrole

HRID 908024Notes

Reaction equation

HRID 908024 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][CH2:11][N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67151710tert-Butyl 4-(4-bromophenyl)-4-oxobutylcarbamate

Product 1

HCID 114246115-(4-Bromophenyl)-3,4-dihydro-2h-pyrroleYield 80.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(4-bromophenyl)-4-oxobutylcarbamate (3.42 g, 10 mmol) was stirred in TFA (10 mL) for 6 hrs. Then 50% NaOH solution was added to the mixture to make pH=13-14, the white precipitate was filtrated, washed with water and dried to give the title compound as a white solid (1.8 g, yield 80%). LC-MS (ESI) m/z: 224 (M+1)+.

Workup

  1. filtrationthe white precipitate was filtrated
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-afb00f572c0242b49d79dded14e357f0
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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