Hydrochloric Acid → (2-Fluoro-4-methoxyphenyl)boronic acid

HRID 1764901Notes

Reaction equation

HRID 1764901 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[F:15].C[O:17][B:18](OC)[O:19]C.Cl>C1COCC1>[F:15][C:8]1[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=1[B:18]([OH:19])[OH:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 37184441-Bromo-2-fluoro-4-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 15789384(2-Fluoro-4-methoxyphenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (1.6 M solution in hexanes, 29.1 mmol, 18.2 mL) was added to 1-bromo-2-fluoro-4-methoxybenzene (24.4 mmol, 5.0 g) in THF (150 mL) at −78° C. under an atmosphere of nitrogen. After stirring for thirty minutes the trimethylborate (95.1 mmol, 10.8 mL) was added over twenty minutes. The reaction was allowed to warm to room temperature overnight while stirring. The solution was then acidified with HCl (3 M, 200 mL), and extracted into EtOAc. The EtOAc was then extracted with NaOH (1 N, 4×100 mL), which was subsequently acidified with concentrated HCl forming (2-fluoro-4-methoxyphenyl) boronic acid as a white precipitate. The white precipitate (2.04 g, 49%) was filtered and dried. 1H NMR (CD3OD, 300 MHz): 7.29 (1H, t, J 8.0 Hz), 6.73 (1H, dd, J 8.5 and 2.2 Hz), 6.62 (1H, dd, J 11.4 and 2.2 Hz), 3.78 (3H, s.)

Workup

  1. additionwas added over twenty minutes
  2. extractionextracted into EtOAc
  3. extractionThe EtOAc was then extracted with NaOH (1 N, 4×100 mL), which

Sources & evidence

ORD record
ord-3e2f0890833d4c9fbda7246bb914f16b
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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