Hydrochloric Acid → HCID 67057732, compound

HRID 604605Notes

Reaction equation

HRID 604605 reaction equation
C([Li])CCC.[C:6]([C:10]1[CH:15]=[C:14](I)[C:13]([O:17][CH3:18])=[CH:12][C:11]=1[F:19])([CH3:9])([CH3:8])[CH3:7].[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C.Cl>C1COCC1>[C:6]([C:10]1[C:11]([F:19])=[CH:12][C:13]([O:17][CH3:18])=[C:14]([B:20]([OH:25])[OH:21])[CH:15]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 67057738HCID 67057738, compoundHCID 178418339Butyllithium

Product 1

HCID 67057732HCID 67057732, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (1.6 M in hexanes, 406 μL, 0.649 mmol) was added to a stirred solution of 1-tert-butyl-2-fluoro-5-iodo-4-methoxybenzene (200 mg, 0.649 mmol) in dry THF (2 mL) at −78° C. under N2. The reaction was stirred at −78° C. for 1 h then triisopropyl borate (214 mg, 262 μL, 1.14 mmol) was added dropwise. The reaction was stirred at −78° C. for 1 h and 0° C. for 1 h. 1N HCl was added and the reaction was extracted with EtOAc (3×). The combined extracts were dried (Na2SO4) and concentrated in vacuo to afford (5-tert-butyl-4-fluoro-2-methoxyphenyl)boronic acid. 1H NMR (600 MHz, CDCl3): δ 6.86 (d, J=8.0 Hz, 1H); 6.57 (d, J=13.0 Hz, 1H); 3-85 (s, 3H); 1.33 (s, 9H).

Workup

  1. stirringThe reaction was stirred at −78° C. for 1 h and 0° C. for 1 h
  2. extractionthe reaction was extracted with EtOAc (3×)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57a711b1d94e4407901475975f0eb929
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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