Boron tribromide → HCID 59402886, compound

HRID 415678Notes

Reaction equation

HRID 415678 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([CH2:12][O:13]CC3C=CC=CC=3)[S:11][C:7]=2[CH:6]=1)=[O:4].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([CH2:12][OH:13])[S:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59402920HCID 59402920, compound

Product 1

HCID 59402886HCID 59402886, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-Benzyloxymethyl-benzothiazole-6-carboxylic acid methyl ester (0.10 g, 0.32 mmol) in 2 ml of DCM was cooled to −78° C. followed by addition of BBr3 (0.06 ml, 0.64 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 (0.08 g, Crude yield).

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-8d3effb594e144b3a085a8020db60d39
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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