Boron tribromide → 287198-05-4

HRID 538555Notes

Reaction equation

HRID 538555 reaction equation
C([O:8][CH2:9][C:10]1[S: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.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[N:14]=[C:10]([CH2:9][OH:8])[S:11][CH:12]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59402770HCID 59402770, compound

Product 1

HCID 2726647287198-05-4Yield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-Benzyloxymethyl-4-(4-chloro-phenyl)-thiazole (2.0 g, 6.34 mmol) in 25 ml of DCM was cooled to −78° C. followed by addition of BBr3 (2.38 ml, 25.3 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. The crude residue was purified over silica gel (60-120 M, 40% EtOAc-Hexane) to get the desired product (0.8 g, 57%). The corresponding cyano derivative was also prepared by the same general method.

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
  6. customThe crude residue was purified over silica gel (60-120 M, 40% EtOAc-Hexane)

Sources & evidence

ORD record
ord-44fa4cb8225544089585eec4376de21a
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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