Isopropanol → 3-Chloro-4-isopropoxybenzonitrile

HRID 1172915Notes

Reaction equation

HRID 1172915 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[OH:29])[C:24]#[N:25].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C(O)(C)C>O1CCCC1>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH:1]([CH3:6])[CH3:2])[C:24]#[N:25]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 2735739Benzonitrile, 3-chloro-4-hydroxy-

Product 1

HCID 595565423-Chloro-4-isopropoxybenzonitrileYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a round bottom flask containing triphenylphosphine (27.3 g, 104 mmol) and 3-chloro-4-hydroxy-benzonitrile (10 g, 65 mmol) was added anhydrous tetrahydrofuran (600 mL). The mixture was stirred briefly under nitrogen, di-tert-butyl azodicarboxylate (24 g, 104 mmol) was then added. The mixture was stirred for a few minutes, followed by addition of anhydrous isopropanol (6.23 mL, 81.4 mmol). The reaction mixture was stirred at room temperature overnight under nitrogen. The crude product was purified by flash chromatography using 1:4 (v/v) ethyl acetate/heptane as eluent. Fractions were dried to give 3-chloro-4-isopropoxy-benzonitrile (12.2 g, 91%) as a red-orange semi-solid.

Workup

  1. stirringThe mixture was stirred for a few minutes
  2. stirringThe reaction mixture was stirred at room temperature overnight under nitrogen
  3. customThe crude product was purified by flash chromatography
  4. customFractions were dried

Sources & evidence

ORD record
ord-ef58206ffeb14dfcbabf24e98f871fc7
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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