(Dimethyl sulfide)trihydroboron → 2,3-Difluoro-4-(2-hydroxyethyl)phenol

HRID 1689396

Reaction equation

HRID 1689396 reaction equation
CSC.B.[F:5][C:6]1[C:11]([F:12])=[C:10]([OH:13])[CH:9]=[CH:8][C:7]=1[CH2:14][C:15](O)=[O:16]>O1CCCC1>[F:12][C:11]1[C:6]([F:5])=[C:7]([CH2:14][CH2:15][OH:16])[CH:8]=[CH:9][C:10]=1[OH:13]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 299221072-(2,3-Difluoro-4-hydroxyphenyl)acetic acid

Product 1

HCID 534161452,3-Difluoro-4-(2-hydroxyethyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane dimethylsulfide complex (2M in THF, 14.4 mL) was added dropwise to a solution of 2-(2,3-difluoro-4-hydroxyphenyl)acetic acid (example 77, step a) (1.08 g) in tetrahydrofuran (25 mL) at 0° C. and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with methanol and when bubbling had ceased the solvent evaporated. The residue was purified by silica gel chromatography eluting with 4:1 isohexane:ethyl acetate to ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as white solid. Yield 0.95 g.

Workup

  1. customThe reaction was quenched with methanol and when
  2. custombubbling
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 4:1 isohexane
  6. additionThe fractions containing product
  7. customevaporated

Sources & evidence

ORD record
ord-4d3caea8e3284c38a3665431d788b75d
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Linked notes

Loading…