(3-Chlorophenyl)boronic acid → HCID 86602804, compound

HRID 2243883Notes

Reaction equation

HRID 2243883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.C([O-])(=O)C.[Cl:19][C:20]1[CH:21]=[C:22]([I+2:26])[CH:23]=[CH:24][CH:25]=1.[F:27][B-:28]([F:31])([F:30])[F:29].[Na+]>C(Cl)Cl>[F:27][B-:28]([F:31])([F:30])[F:29].[Cl:1][C:2]1[CH:3]=[C:4]([I+:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2734323(3-Chlorophenyl)boronic acidHCID 4343483Sodium TetrafluoroborateHCID 178476552HCID 178476552, compound

Product 1

HCID 86602804HCID 86602804, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Borontrifluoride diethyl etherate (16.51 g, 116.3 mmol) was added slowly to 3-chlorophenyl boronic acid (17.37 g, 111.0 mmol) in DCM (170 mL) at −5° C., while stirring. After 15 minutes, the title compound of Example 15.1 (37.71 g, 105.8 mmol) in DCM (150 mL) was added slowly. The reaction stirred for 1 h at 0° C. and sodium tetrafluoroborate (225 g in 300 mL water) was added and stirred for 1 h. The organic layer was separated, dried over sodium sulphate, filtered and concentrated and triturated with ether to afford the title product (31.6 g, 68%) as a light brown solid.

Workup

  1. stirringThe reaction stirred for 1 h at 0° C.
  2. stirringstirred for 1 h
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customtriturated with ether

Sources & evidence

ORD record
ord-eeadb29e8044426aa6ad24623394238f
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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