1-Bromo-4-isopropylbenzene → (5-Allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanol

HRID 1046381Notes

Reaction equation

HRID 1046381 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([Mg]Br)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Mg].BrC1C=CC(C(C)C)=CC=1.[CH2:23]([O:26][C:27]1[CH:28]=[CH:29][C:30]([N+:35]([O-:37])=[O:36])=[C:31]([CH:34]=1)[CH:32]=[O:33])[CH:24]=[CH2:25].[Cl-].[NH4+]>C1COCC1>[CH2:23]([O:26][C:27]1[CH:28]=[CH:29][C:30]([N+:35]([O-:37])=[O:36])=[C:31]([CH:32]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)[OH:33])[CH:34]=1)[CH:24]=[CH2:25]

Participants

7

Reactant 5

HCID 114621-Bromo-4-isopropylbenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 592590815-Allyloxy-2-nitrobenzaldehydeHCID 178439193HCID 178439193, compound

Product 1

HCID 59259038(5-Allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-isopropylphenylmagnesium bromide prepared from 2.35 g (96.5 mmol) magnesium and 18.15 g (96.5 mmol) 1-bromo-4-isopropylbenzene in 80 ml THF is added slowly at −78° C. to a solution of 20 g (96.5 mmol) 5-allyloxy-2-nitro-benzaldehyde in 200 ml THF. After allowing the reaction mixture to warm up to r.t. saturated aqueous ammonium chloride solution is added. Extraction with ethyl acetate followed by chromatographic purification on silica (hexane/ethyl acetate) yields (5-allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanol.

Workup

  1. additionis added
  2. extractionExtraction with ethyl acetate
  3. customfollowed by chromatographic purification on silica (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f207a885c7864ff19f59d437910e44a9
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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