Water → 1-Bromo-4-(1-propynyl)benzene

To a solution of 1-bromo-4-ethynyl-benzene (500 mg, 2.8 mmol) in tetrahydrofuran (20 mL) at −30° C. was slowly added sodium bis(trimethylsilyl)amide in tetrahydrofuran solution (1M, 4.2 mL). After stirring 15 min, methyl iodide (1.1 g, 8.4 mmol) was added at −20° C. The resulting reaction mixture was stirred at RT for 50 min before it was added to water. The mixture was extracted with ethyl acetate and the organic phase was dried over magnesium sulfate and concentrated. The crude product 1-bromo-4-prop-1-ynyl-benzene was obtained as a volatile liquid (450 mg, 82.8% yield) which was put to next step directly without further purification. 1H NMR (400 MHz, MeOD) δ ppm 7.34 (d, J=8.3 Hz, 10H), 7.14 (d, J=8.3 Hz, 10H), 1.91 (s, 3H); GCMS, (M+1)=195.1, Molecular Formula=C9H7Br.

1. customat −30° C.
2. customThe resulting reaction mixture
3. stirringwas stirred at RT for 50 min before it
4. extractionThe mixture was extracted with ethyl acetate
5. dry with materialthe organic phase was dried over magnesium sulfate
6. concentrationconcentrated

ORD record

ord-4a9cc71918ba42e9b0a3dd1220215038

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426414B2