tert-Butanol → HCID 81550815, compound

HRID 2420766Notes

Reaction equation

HRID 2420766 reaction equation
C([Li])CCC.CCCCCC.[C:12]([OH:16])([CH3:15])([CH3:14])[CH3:13].[Br:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21](Cl)=[O:22]>C1COCC1.CCOCC>[Br:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:22]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8058HexaneHCID 79018185HCID 79018185, compoundHCID 178418339Butyllithium

Product 1

HCID 81550815HCID 81550815, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium in hexane (12.8 mL of 2.5 M, 32 mmol) is added with stirring to t-butanol (46 mL) at 25° C. under an argon atmosphere. After 30 min the mixture is treated dropwise with a solution of 3-bromo-5-nitro-benzoyl chloride (J. Mindl, Collect. Czech. Chem. Commun. (1973), 38, 3496-505; 32 mmol) in dry THF (40 mL) and stirred for a further 17 h. The mixture is then treated with ether (250 mL) and washed with brine. The ether solution was dried (MgSO4) and the solvent is evaporated off under reduced pressure to give the crude product which is purified by column chromatography (silica gel, eluent 20% ethyl acetate in hexane) and recrystallised from ether-hexane to afford the title compound as colourless crystalline solid, m.p. 77-78° C.

Workup

  1. washwashed with brine
  2. dry with materialThe ether solution was dried (MgSO4)
  3. customthe solvent is evaporated off under reduced pressure
  4. customto give the crude product which
  5. customis purified by column chromatography (silica gel, eluent 20% ethyl acetate in hexane)
  6. customrecrystallised from ether-hexane

Sources & evidence

ORD record
ord-5be36b82f03246ca8dd49d6b8795472c
Source dataset
uspto-grants-2011_06
Patent number
US07956053B2

Reaction notes

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