4-Nitrobenzyl bromide → HCID 67486784, compound

HRID 2371270Notes

Reaction equation

HRID 2371270 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[N+:30]([C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)([O-:32])=[O:31]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:21])[CH:10]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:13][CH:12]=1)[CH2:37][C:36]1[CH:39]=[CH:40][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 2724682Lithium diisopropylamideHCID 67486384HCID 67486384, compound

Product 1

HCID 67486784HCID 67486784, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (4-tert-Butyl-phenyl)-acetic acid benzyl ester (92 g, 7.1 mmol) in tetrahydrofuran (50 ml) was added lithium diisopropylamide (8.5 mmol) at −78° C. After 30 min, 4-nitrobenzyl bromide (1.6 g, 7.5 mmol) was added. The cold bath was removed and the reaction mixture was allowed to warm to ambient temperature in 1 h. The reaction mixture was concentrated, partitioned between ethyl acetate and 1N ammonium chloride, washed with water, and dried over magnesium sulfate. Chromatography of the residue (5% ethyl acetate in hexane) afforded 2-(4-tert-Butyl-phenyl)-3-(4-nitro-phenyl)-propionic acid benzyl ester as a yellow oil (2.46, 83%).

Workup

  1. customThe cold bath was removed
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and 1N ammonium chloride
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-147c8d94c8d541f29e227f61244d902f
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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