Benzyl Bromide → HCID 11143141, compound

Temperature

0 °C

1,3-Dimethoxy-5-bromobenzene (14.5 g, 66.7 mmol) was dissolved in 40 mL CH2Cl2 and cooled to 0° C. BBr3 (100 mL, 1.0 M in CH2Cl2, 100 mmol) was added and the solution was stirred for 12 h at room temperature. The reaction was carefully quenched with MeOH and then concentrated to dryness. The resulting syrup was redissolved in EtOAc and was washed with H2O (3×25 mL). The organic phase was then dried over Na2SO4, filtered and concentrated to dryness. The residue was then dissolved in DMF (50 mL) and K2CO3 (20.2 g, 146.7 mmol) was added, followed by benzyl bromide (BnBr, 17.4 mL, 146.7 mmol). The reaction mixture was stirred for 3 h after which TLC analysis (60% EtOAc/hexanes) indicated that the reaction was complete. The reaction mixture was then diluted in EtOAc and washed with water (3×50 mL). The organic phase was dried over Na2SO4, filtered and concentrated to yield the crude product. The product was crystallized from isopropanol to yield 1,3-bis-Benzyloxy-5-bromobenzene 22 (21 g, 57 mmol, 85° A) yield) as a white powder. 1H NMR (CD2Cl2) δ 7.3-7.5 (m, 10H), 6.71 (s, 2H), 6.60 (s, 1H), 5.05 (s, 4H); 13C NMR (CD2Cl2) δ 161.2, 137.2, 128.9, 128.4, 127.8, 123.1, 111.0, 101.5, 70.0.

1. customThe reaction was carefully quenched with MeOH
2. concentrationconcentrated to dryness
3. dissolutionThe resulting syrup was redissolved in EtOAc
4. washwas washed with H2O (3×25 mL)
5. dry with materialThe organic phase was then dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated to dryness
8. dissolutionThe residue was then dissolved in DMF (50 mL)
9. washwashed with water (3×50 mL)
10. dry with materialThe organic phase was dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customto yield the crude product
14. customThe product was crystallized from isopropanol

ORD record

ord-161ca10443424c318abba624c53d5e23

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000050B2