Hydrochloric Acid → 2-(4-Iodophenyl)-3-methylbutan-2-ol

HRID 2092128Notes

Reaction equation

HRID 2092128 reaction equation
C([Li])CCC.I[C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1.[CH3:14][CH:15]([CH3:19])[C:16](=[O:18])[CH3:17].Cl>C1COCC1>[I:13][C:10]1[CH:11]=[CH:12][C:7]([C:16]([OH:18])([CH:15]([CH3:19])[CH3:14])[CH3:17])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 112513-Methyl-2-butanoneHCID 12208p-DiiodobenzeneHCID 178418339Butyllithium

Product 1

HCID 590267482-(4-Iodophenyl)-3-methylbutan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (37.0 mL of a 2.5 M solution in hexanes, 92.8 mmol) was added to a stirred solution of 1,4-diiodobenzene (30.0 g, 90.9 mmol) in THF (200 mL) at −78° C. After approximately 20 min, 3-methyl-2-butanone (10.2 mL, 95.5 mmol) was added, and the resulting mixture was allowed to stir at −78° C. for about 1 h. The reaction mixture was poured into aqueous 1N HCl and extracted twice with diethyl ether. The combined organic extracts were washed water and brine, dried (magnesium sulfate) and concentrated in vacuo to afford the title compound i-2a. m/z (ES) 273 (M-OH)+. 1HNMR (500 MHz, CDCl3): δ 7.67 (d, 2H, J=8.5 Hz), 7.20 (d, 2H, J=8.7 Hz), 2.00 (m, 1H), 1.52 (s, 3H), 0.92 (d, 3H, J=6.7 Hz), 0.81 (d, 3H, J=6.9 Hz).

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe combined organic extracts were washed water and brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-560d4933f0294693a5e48cb456483f96
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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