Hydrochloric Acid → HCID 86685089, compound

HRID 1750845Notes

Reaction equation

HRID 1750845 reaction equation
[F:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[O:8][B:7]([OH:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:14].C(OOC(=O)C1C=CC=CC=1)(=[O:22])C1C=CC=CC=1.C1C(=O)N(Br)C(=O)C1.C([O-])([O-])=O.[Na+].[Na+].Cl>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[C:10]2[C:9]([CH3:11])([CH3:12])[O:8][B:7]([OH:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:14]=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7187Benzoyl PeroxideHCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 86685087HCID 86685087, compound

Product 1

HCID 86685089HCID 86685089, compoundYield 661.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (970 mg, 5 mmol) in CCl4 (50 mL) at rt was added benzoyl peroxide (121 mg, 0.5 mmol) followed by NBS (1.958 g, 11.0 mmol). The reaction mixture was heated under reflux for 16 h, cooled to rt and treated with Na2CO3. The aqueous layer was acidified with 3 N HCl to pH 3 and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (2:1) to give 4-fluoro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (688 mg, 68%) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 h
  3. extractionextracted three times with ethyl acetate
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluted with PE-EA (2:1)

Sources & evidence

ORD record
ord-a217b68af1ef4810899404773000ed1f
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

Loading…