Boron tribromide → HCID 59402814, compound

HRID 538585Notes

Reaction equation

HRID 538585 reaction equation
C(O[CH2:9][C:10]1[O:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:14]=1)C1C=CC=CC=1.B(Br)(Br)[Br:23].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:23][CH2:9][C:10]1[O:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:14]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59402951HCID 59402951, compound

Product 1

HCID 59402814HCID 59402814, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-Benzyloxymethyl-4-(4-chloro-phenyl)-oxazole (1.10 g, 3.6 mmol) in 10 ml of DCM was cooled to −78° C. followed by addition of BBr3 (1.76 ml, 18.0 mmol). The reaction mixture was stirred at 25° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), solution of NaHCO3 (20 mL) was added at 0° C. and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to get the desired product (0.5 g, 49%, crude).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea94400bafa44507b4fd49b20bf5d135
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

Loading…