Benzene, 1-chloro-4-fluoro- → (5-Chloro-2-fluoro-phenyl)boronic acid

HRID 1768478Notes

Reaction equation

HRID 1768478 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C([Li])CCC.[B:14](OC(C)C)([O:19]C(C)C)[O:15]C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([B:14]([OH:19])[OH:15])[CH:3]=1

Participants

5

Reactant 3

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 21531Triisopropyl borateHCID 178418339Butyllithium

Product 1

HCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 30.0 g (23 mmol) of 1-chloro-4-fluorobenzene in THF at −78° C. was added 14.4 mL (23 mmol) of a n-butyllithium solution (1.6M in hexanes). After stirring for 2.5 h at that temperature, 10.6 mL (46 mmol) of triisopropyl borate was added dropwise, and the reaction was allowed to slowly warm to room temperature and stir overnight. The reaction was carefully quenched with 1M HCl and then extracted three times with Et2O. The combined organic phase was washed with water, dried over MgSO4, and concentrated to provide 20-1 as a white powder. Data for 20-1: 1HNMR (500 MHz, CDCl3) δ 7.8 (m, 1H), 7.4 (m, 1H), 7.0 (m, 1H), 5.2 (m, 2H) ppm.

Workup

  1. additionwas added dropwise
  2. customThe reaction was carefully quenched with 1M HCl
  3. extractionextracted three times with Et2O
  4. washThe combined organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fb00007b8ab40e7a1465f85d4ed739a
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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