Boron tribromide → HCID 11449072, compound

HRID 2084836Notes

Reaction equation

HRID 2084836 reaction equation
C([O:5][C:6](=[O:24])[CH:7]([N:11]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:12])[CH:8]([CH3:10])[CH3:9])(C)(C)C.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:11]([CH3:12])[C@H:7]([CH:8]([CH3:9])[CH3:10])[C:6]([OH:24])=[O:5])(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 69801848HCID 69801848, compound

Product 1

HCID 11449072HCID 11449072, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° solution of 0.707 g (1.980 mmol) of the product of Example 5 in 50 mL of dichloromethane was added 9.4 mL (9.395 mmol) of a 1.0M solution of boron tribromide in dichloromethane. The resulting mixture was stirred at 0° for 0.5 h and then warmed to room temperature and stirred for an additional 4 h. The reaction mixture was then poured into a saturated sodium bicarbonate solution and extracted with dichloromethane. The aqueous layer was acidified with 5% HCl solution and extracted with dichloromethane. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1) to provide 0.271 g (48%) of the phenolcarboxylic acid as a colorless oil. Electrospray Mass Spec: 287.9 (M+H)+.

Workup

  1. stirringstirred for an additional 4 h
  2. extractionextracted with dichloromethane
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-10bbb56629eb4a949b2b604491e3f413
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

Loading…