Trimethyl borate → HCID 58788855, compound

In dried glassware, 2.5M n-BuLi in hexanes (18.01 mL, 45.02 mmol) was added over 15 minutes to a stirred solution of 1-ethoxy-4-fluoro-5-iodo-2-methyl-benzene [CAS: 918813-06-6](9.7 g, 34.63 mmol) in dry THF (100 mL) at −78° C. under N2. After stirring for 30 mins, trimethyl borate (7.72 mL, 69.27 mmol) was added over 10 mins. The mixture was stirred for 3.25 h at −78° C. then quenched by slow addition of 1M HCl (115 ml). The mixture was warmed to ambient temperature, diluted with water (115 ml) and extracted with EtOAc (2×100 ml). The combined organic extracts were washed with saturated sodium metabisulfite soln (250 ml), brine (100 ml) and dried (MgSO4). The almost colourless solution was evaporated to a cream solid, dried rt/vac/1 h (wt=6.2 g). This solid was stirred with Et2O/iso-hexane (1:1) (40 ml) and filtered under suction and washed with the mixture then iso-hexane, dried rt/vac/overnight to give (5-ethoxy-2-fluoro-4-methyl-phenyl)boronic acid (D94) (4.0 g);

1. stirringThe mixture was stirred for 3.25 h at −78° C.
2. customthen quenched by slow addition of 1M HCl (115 ml)
3. additiondiluted with water (115 ml)
4. extractionextracted with EtOAc (2×100 ml)
5. washThe combined organic extracts were washed with saturated sodium metabisulfite soln (250 ml), brine (100 ml)
6. dry with materialdried (MgSO4)
7. customThe almost colourless solution was evaporated to a cream solid
8. customdried rt/vac/1 h (wt=6.2 g)
9. stirringThis solid was stirred with Et2O/iso-hexane (1:1) (40 ml)
10. filtrationfiltered under suction
11. washwashed with the mixture
12. dry with materialiso-hexane, dried rt/vac/overnight

ORD record

ord-b05036fa94b54fc79ee764610af88967

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376436B2