4-Bromoanisole → 1-(4-Bromobutyl)-4-methoxybenzene

After starting the Grignard reaction by adding 5.00 ml 4-bromoanisole to a mixture of 4.86 g (0.20 mol) magnesium turnings and 100 ml THF, 20.00 ml 4-bromoanisole (total: 25.0 ml (37.4 g; 0.20 mol) were added at a pace sufficient to maintain reflux temperature. The reaction mixture was heated to reflux for additional 3 h, cooled to r.t. and dropped at 0° C. within 1 h to a stirred solution prepared by mixing 129.6 g (71.6 ml, 0.60 mol) 1,4-dibromo-butane in 200 ml THF with a freshly prepared solution of 0.17 g (4.0 mmol) LiCl and 0.267 g (2.0 mmol) Cu(II)Cl2 in 20 ml THF. Stirring was continued for 12 h at r.t. followed by the addition of 100 ml of a 20% ammonium chloride solution and 200 ml ethyl acetate. The water phase was extracted twice with 50 ml ethyl acetate, all organic phases were combined, dried over sodium sulphate and evaporated. The resulting oil was fractionated by vacuum distillation. Yield: 27.7 g (57%), b.p. 112–115° C./0.15 mbar.

1. customthe Grignard reaction
2. addition25.0 ml (37.4 g; 0.20 mol) were added at a pace sufficient
3. temperatureto maintain
4. temperaturereflux temperature
5. temperatureThe reaction mixture was heated
6. temperatureto reflux for additional 3 h
7. additiondropped at 0° C. within 1 h to a stirred solution
8. customprepared
9. extractionThe water phase was extracted twice with 50 ml ethyl acetate
10. dry with materialdried over sodium sulphate
11. customevaporated
12. distillationThe resulting oil was fractionated by vacuum distillation

ORD record

ord-bf724c81354f4028bb494a566e952a8e

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07235574B2