Trifluoroacetic acid → [4-Fluoro-2-(hydroxymethyl)phenyl]boronic acid

HRID 1773646Notes

Reaction equation

HRID 1773646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[C:4]([CH2:11][O:12][Si](C(C)C)(C(C)C)C(C)C)[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:9])[OH:10])=[C:4]([CH2:11][OH:12])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66692124HCID 66692124, compound

Product 1

HCID 24964133[4-Fluoro-2-(hydroxymethyl)phenyl]boronic acidYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 2.60 g (7.97 mmol) (4-fluoro-2-{[(triisopropylsilyl)oxy]methyl}phenyl)boronic acid which was prepared according to intermediate example 299b in 10 mL dichloromethane were added 6.14 mL trifluoroacetic acid and the mixture was stirred for 16 hours at 23° C. The solvent was removed and the residue crystallized from n-hexane to give 682 mg (50%) of the title compound.

Workup

  1. customThe solvent was removed
  2. customthe residue crystallized from n-hexane

Sources & evidence

ORD record
ord-90020ba72c3c4f8a902413b06d95e8fa
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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