Chloromethyl Methyl Ether → 1-Bromo-4-chloro-5-(4-ethylbenzyl)-2-((methoxymethoxy)methyl)benzene

To a cooled (0° C.) solution of (2-bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol (4.0 g, 11.8 mmol) in CH2Cl2 (60 mL), was added N,N-Diisopropylethylamine (DIPEA) (10.5 mL, 59.0 mmol) and MOMCl (4.5 μL, 59.0 mmol) successively. The reaction mixture was kept at 0° C. for 1 h, and then warmed to room temperature and kept at that temperature for 4 h. The reaction was quenched with H2O, the organic layer was separated and the aqueous layer was extracted 2× with CH2Cl2. The combined organic layers were washed 1× with brine prior to drying over Na2SO4. The volatiles were removed using a rotary evaporator and the resulting residue was purified by a silica gel column (50:1 petroleum ether:ethyl acetate as eluent) to give 4.05 g of pure product as colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.52 (s, 1H), 7.33 (s, 1H), 7.12 (q, 4H), 4.77 (s, 2H), 4.60 (s, 2H), 4.03 (s, 2H), 3.44 (s, 3H), 2.64 (q, J=7.5 Hz, 2H), 1.24 (t, J=7.5 Hz, 3H).

1. waitkept at that temperature for 4 h
2. customThe reaction was quenched with H2O
3. customthe organic layer was separated
4. extractionthe aqueous layer was extracted 2× with CH2Cl2
5. washThe combined organic layers were washed 1× with brine
6. dry with materialto drying over Na2SO4
7. customThe volatiles were removed
8. customa rotary evaporator
9. customthe resulting residue was purified by a silica gel column (50:1 petroleum ether:ethyl acetate as eluent)

ORD record

ord-a6511d3c82ad4b509b02e433ead99250

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803778B2