1,5-Dibromopentane → 4-[6-Bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene

HRID 863884Notes

Reaction equation

HRID 863884 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[O:18][CH3:19].C([Li])(C)(C)C.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br>O1CCCC1>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:18][CH3:19])[CH:5]=1)[S:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 105164711,2-Dimethoxy-4-[[(4-methylphenyl)thio]methyl]benzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 108122034-[6-Bromo-1-[(4-methylphenyl)thio]hexyl]-1,2-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13.72 g of 1,2-dimethoxy-4-[[(4-methylphenyl)thio]methyl]benzene in 200 mL of tetrahydrofuran (dried over 3A sieves), under nitrogen, is cooled to -78° C. and 30 mL of 1.7M t-butyl lithium is added. After 30 minutes, the solution is transferred, via a canula, into a stirred solution of 14.0 mL of 1,5-dibromopentane in 25 ml of tetrahydrofuran, under nitrogen at -78° C. The reaction is slowly warmed to room temperature, and the reaction is quenched by the addition of 4 mL of acetone. The reaction is concentrated in vacuo and the residual material is dissolved in ethyl acetate and is washed with brine. Drying (sodium sulfate) and solvent removal affords 33.22 g of oil. The residue is purified via chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol to afford 10.82 g of the desired product as a tan gum. MS(FAB): m/z 299(M-TolSH).

Workup

  1. customthe reaction is quenched by the addition of 4 mL of acetone
  2. concentrationThe reaction is concentrated in vacuo
  3. dissolutionthe residual material is dissolved in ethyl acetate
  4. washis washed with brine
  5. customDrying
  6. custom(sodium sulfate) and solvent removal

Sources & evidence

ORD record
ord-311ff8a820cf44fcbd453ac0c60e513c
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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