Hydrochloric Acid → 4-Hexyloxy-2-fluorophenylboronic acid

HRID 327366Notes

Reaction equation

HRID 327366 reaction equation
C([Li])CCC.[CH2:6]([O:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([F:20])[CH:14]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C([O:24][B:25](OC(C)C)[O:26]C(C)C)(C)C.Cl>C1COCC1>[CH2:6]([O:12][C:13]1[CH:18]=[CH:17][C:16]([B:25]([OH:26])[OH:24])=[C:15]([F:20])[CH:14]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 191078664-n-Hexyloxy-2-fluorobromobenzeneHCID 178418339Butyllithium

Product 1

HCID 230054294-Hexyloxy-2-fluorophenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-butyllithium (10.0M in hexane, 3.30 ml) is added dropwise to a stirred cooled (-78° C.) solution of 3A (9.0 g) in dry THF (70 ml) under dry N2. The stirred mixture is maintained under these conditions for 2.5 h and then a cooled solution of tri-isopropylborate (11.28 g) in dry THF (50 ml) is added dropwise at -78° C. The stirred mixture is allowed to warm to room temperature overnight and then stirred for 1 h at room temperature with 10 HCl (50 ml). The product is extracted into ether twice and the combined ethereal extracts are washed with water and dried (MgSO4). The solvent is removed in vacuo to afford an off-white solid.

Workup

  1. temperatureThe stirred mixture is maintained under these conditions for 2.5 h
  2. extractionThe product is extracted into ether twice
  3. washthe combined ethereal extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent is removed in vacuo
  6. customto afford an off-white solid

Sources & evidence

ORD record
ord-e034c326cebf4cf1927e3511edcb4724
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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