Triphenylphosphine → HCID 58902319, compound

HRID 1640151Notes

Reaction equation

HRID 1640151 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([CH2:33]O)[CH:32]=1)[C:27]([OH:29])=[O:28])([CH3:23])([CH3:22])[CH3:21].Br[N:36]1[C:40](=O)[CH2:39][CH2:38][C:37]1=O.N1CCCC1>CC(C)=O.O.CCOC(C)=O>[C:20]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([CH2:33][N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH:32]=1)[C:27]([OH:29])=[O:28])([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 31268PyrrolidineHCID 67184N-bromobutanimideHCID 58902281HCID 58902281, compound

Product 1

HCID 58902319HCID 58902319, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of triphenylphosphine (1.2 g, 0.0048 mol) and 3-tert-butyl-5-(hydroxymethyl)benzoic acid (1.0 g, 0.0048 mol) in acetone (20 mL) at −18° C. was added N-bromosuccinimide (0.85 g, 0.0048 mol) portionwise over 2 minutes. After 5 minutes, pyrrolidine (0.96 mL, 0.012 mol) was added. The reaction mixture was heated at 80° C. overnight. EtOAc and water were added to the reaction mixture. The phases were separated and the organic solution was washed with 1M NaOH, 1M HCl, and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give 3-tert-butyl-5-(pyrrolidin-1-ylmethyl)benzoic acid (6%). LCMS ES+ 262, ES− 260.

Workup

  1. customThe phases were separated
  2. washthe organic solution was washed with 1M NaOH, 1M HCl, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-02a7ec97c5334a8d984ef94cceed59ef
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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