Hydrochloric Acid → (3-Fluoro-4-propoxyphenyl)boronic acid

HRID 1600935Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[C:9]([F:17])[CH:8]=1.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.Cl>O1CCCC1>[F:17][C:9]1[CH:8]=[C:7]([B:18]([OH:23])[OH:19])[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution n-butyllithium (2.5 M in hexanes, 4.4 ml) was added dropwise over 5 minutes to a stirring solution of 1-bromo-3-fluoro-4-propoxybenzene (2.3 g) in tetrahydrofuran (10 ml) at -70° C. The solution was stirred at -70° C. for 15 minutes and then transferred by cannula to a solution of triisopropyl borate (4.14 g) in tetrahydrofuran (10 ml) at -78° C. Once addition was complete the mixture was stirred at room temperature for 30 minutes. A solution of dilute hydrochloric acid (2 M, 30 ml) was added and the mixture extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the sub-title compound as a white solid (1.19 g).

Workup

additionOnce addition
stirringwas stirred at room temperature for 30 minutes
extractionthe mixture extracted with ethyl acetate (3×50 ml)
dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8607aaf3647f483d80d3e04c4509976e
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977105

Reaction notes

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