ChemicalBook CAS DataBase List 2-Bromo-5-methoxytoluene

2-Bromo-5-methoxytoluene synthesis

13synthesis methods

Product Name:2-Bromo-5-methoxytoluene
CAS Number:27060-75-9
Molecular formula:C8H9BrO
Molecular Weight:201.06

74-88-4
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$15.00/10g

27060-75-9
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$8.00/5g

Yield:27060-75-9 75%

Reaction Conditions:

Stage #1:4-bromo-3-methylphenol with potassium carbonate in N,N-dimethyl-formamide at 20; for 0.0833333 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 24 h;

Steps:

l-Bromo-4-methoxy-2-methyl-benzene 88. To a stirred solution of of 4-bromo-3 -methyl phenol (1 g, 5.3 mmol) in 6 mL DMF was added K₂CO₃ (2.21g, 16 mmol) and the reaction was stirred at r.t. for 5 min before addition of MeI (0.41 mL, 6.6 mmol). Stirring was continued for a further 24 h before water was added and the organics were extracted into EtOAc. The solution was concentrated under reduced pressure to give pale brown liquid, 0.814 g, 75% yield: ¹H NMR (270 MHz, CDCl₃) 2.36 (3H, s), 3.76 (3H, s), 6.61 (IH₅ dd, J= 3.0, 8.8 Hz)₅ 6.78 (IH₅ d, J= 3.0 Hz), 7.39 (IH, d, J= 8.7 Hz).

References:

STERIX LIMITED WO2007/96647, 2007, A2 Location in patent:Page/Page column 127-128

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100-84-5 Synthesis