Sodium borohydride → HCID 57969111, compound

HRID 1471515Notes

Reaction equation

HRID 1471515 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([B:19]2[O:23][C:22](C)(C)C(C)(C)[O:20]2)=[C:15](C=O)[CH:14]=1)[C:5]([O:7][CH3:8])=[O:6].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]2[B:19]([OH:20])[O:23][CH2:22][C:17]=2[CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57969171HCID 57969171, compound

Product 1

HCID 57969111HCID 57969111, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-fluoro-4-(3-formyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzoate (5 g, 12.5 mmol) in MeOH (125 mL) was added NaBH4 (709 mg; 18.75 mmol) in portions under N2 at 0° C. in an ice-bath. The reaction was stirred at 0° C. to room temperature. The reaction was monitored with TLC and was completed overnight. The mixture was cooled to rt. Solvent was evaporated to half volume via Rota vapor. The mixture was then cooled to 0° C., and quenched by adding water (12 mL) following by adding 6 N HCl (12 mL). Stirred at rt for 30 min, white Solid precipitated out. Filtered. The solid was gummy. The solid was suspended in water, sonicated for 1 hr. Filtered, washed with more water. Filtered, dried to get target compound as a white solid (2.1 g, 56%).

Workup

  1. customSolvent was evaporated to half volume via Rota vapor
  2. temperatureThe mixture was then cooled to 0° C.
  3. customquenched
  4. additionby adding water (12 mL)
  5. additionby adding 6 N HCl (12 mL)
  6. stirringStirred at rt for 30 min
  7. customwhite Solid precipitated out
  8. filtrationFiltered
  9. customsonicated for 1 hr
  10. filtrationFiltered
  11. washwashed with more water
  12. filtrationFiltered
  13. customdried

Sources & evidence

ORD record
ord-b30349f4f0e945d39854530f9bd84d49
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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