ChemicalBook CAS DataBase List 6-broMo-2-Methylbenzo[b]thiophene

6-broMo-2-Methylbenzo[b]thiophene synthesis

5synthesis methods

Product Name:6-broMo-2-Methylbenzo[b]thiophene
CAS Number:912332-92-4
Molecular formula:C9H7BrS
Molecular Weight:227.12

74-88-4
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912332-92-4
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$220.00/50mg

Yield:912332-92-4 95%

Reaction Conditions:

Stage #1: 6-bromobenzo[b]thiophenewith n-butyllithium;N,N,N,N,-tetramethylethylenediamine;N,N-diisopropylamine in tetrahydrofuran at -78 - 0; for 1 h;
Stage #2: iodomethane in tetrahydrofuran;2-methoxy-2-methylpropane at -78 - 20;

Steps:

104.B

Into a stirred solution of 3-bromothiophenol (50.09 g, 264.9 mmol) and K₂CO₃ (36.61 g, 264.9 mmol) in acetone (361 mL) is added bromoacetaldehyde diethyl acetal (39.85 mL, 264.9 mmol) in a dropwise manner. After stirring for 2 h, the resulting slurry is filtered through a sintered glass funnel and the filtrate is concentrated under reduced pressure. The resulting precipitate is diluted with CH₂Cl₂ (200 mL), dried over MgSO₄, EPO filtered and concentrated under reduced pressure to give 3-bromobenzenethio- acetaldehyde diethyl acetal as a yellow oil used in the next step as is (76.83 g, 95%).

References:

WO2006/107784,2006,A1 Location in patent:Page/Page column 135

17347-32-9 Synthesis