Water → 1-Bromo-4-(methoxymethoxy)benzene

Temperature

0 °C

To a suspension of 60% NaH in mineral oil (12.7 g, 31.8 mmol) in anhydrous THF (300 mL) at 0° C. was added 4-bromophenol (50.0 g, 28.9 mmol) dissolved in THF (100 mL) dropwise over 1 h. The reaction mixture was stirred at 0° C. for 30 min, and chloromethylmethyl ether (24.8 mL, 32.6 mmol) dissolved in THF (30 mL) was added dropwise over 20 min. The reaction mixture was stirred overnight at RT. H2O (250 mL) was added, and the mixture was extracted with Et2O (2×250 mL). The combined ethereal extracts were washed with brine (500 mL), dried over MgSO4, and concentrated. The residue was distilled under vacuum to afford 57.6 g (92%) of 13 as a colorless oil. 1H NMR (400 MHz, DMSO-d6): δ 3.33 (s, 3H), 5.15 (s, 2H), 6.96 (d, J=9.0 Hz, 2H), 7.43 (d, J=9.0 Hz, 2H).

1. additionwas added dropwise over 20 min
2. stirringThe reaction mixture was stirred overnight at RT
3. extractionthe mixture was extracted with Et2O (2×250 mL)
4. washThe combined ethereal extracts were washed with brine (500 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. distillationThe residue was distilled under vacuum

ORD record

ord-f97b05abb8034fc896f5f0008f923ca9

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442833B2