Hexane → HCID 67079158, compound

HRID 1047408Notes

Reaction equation

HRID 1047408 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[CH:9]([O:12][CH:13]([CH3:15])[CH3:14])[O:10][CH3:11].C([Li])CCC.CCCCCC.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(OC)(C)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([O:12][CH:13]([CH3:15])[CH3:14])[O:10][CH3:11]

Participants

7

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 67079339HCID 67079339, compoundHCID 178418339Butyllithium

Product 1

HCID 67079158HCID 67079158, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Condition 4: Under a nitrogen atmosphere, 2,4-dibromo-1-(1-methoxy-1-methylethoxymethyl)benzene (500 mg, 1.48 mmol) was dissolved in toluene (3.65 ml) and t-butylmethyl ether (0.35 ml). To the solution was added dropwise n-butyllithium in hexane (1.6 M, 1.01 ml, 1.62 mmol) at 0° C. over 30 minutes. After completion of the addition, a saturated aqueous solution of ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a product containing 4-bromide and 2-bromide as an oil (373 mg). According to 1H-NMR analysis of the product, the ratio of 4-bromide:2-bromide was determined as 40:1, which was calculated based on the integration ratio of peaks of protons at benzyl position.

Workup

  1. additionAfter completion of the addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give a product

Sources & evidence

ORD record
ord-7b23186838594b9995969df569b2e1f6
Source dataset
uspto-grants-2013_10
Patent number
US08569520B2

Reaction notes

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