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

HRID 1968656Notes

Reaction equation

HRID 1968656 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, brine, dried (magnesium sulfate) and concentrated in vacuo to afford the title compound i-3a. 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, J=6.7 Hz), 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, brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e53455b3ad174e5fb5d5374c995636a6
Source dataset
uspto-grants-2013_04
Patent number
US08426413B2

Reaction notes

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