Sodium methanethiolate → 1-Bromo-3-(4-methoxy-benzyloxy)-5-methylsulfanyl-benzene

HRID 418093Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[C:4](Br)[CH:3]=1.[CH3:19][S-:20].[Na+].C[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:20][CH3:19])[CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

1,3-Dibromo-5-(4-methoxy-benzyloxy)-benzene (4.0 g) was dissolved in DMF (60 mL), followed by addition of sodium thiomethoxide (829 mg). The resulting mixture was stirred at 75° C. for 5 h. Over the period of 4 hours additional amount of sodium methoxide (total 754 mg) was added in two equal portions. When the starting material was completely consumed the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to yield the title compound (2.1 g, 60% yield). HRMS calcd for C15H15O2BrS [M+H]+ 339.0049, observed 339.0047.

Workup

customWhen the starting material was completely consumed the reaction mixture
additionwas diluted with ethyl acetate
washwashed with water and brine
extractionThe organic extract
dry with materialwas dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
custompurified on a silica gel column

Sources & evidence

ORD record: ord-84894ebf32104b1594b26eed74e1807e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093253B2

Reaction notes

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