Water → HCID 68080203, compound

HRID 1508514Notes

Reaction equation

HRID 1508514 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[C:7]([CH2:15][O:16]C)=[N:8][C:9]([S:13][CH3:14])=[N:10][C:11]=1[CH3:12].O>C(Cl)Cl>[Cl:5][C:6]1[C:7]([CH2:15][OH:16])=[N:8][C:9]([S:13][CH3:14])=[N:10][C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86704605HCID 86704605, compound

Product 1

HCID 68080203HCID 68080203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1M BBr3 in CH2Cl2 (9.5 ml, 9.5 mmol) was added to a solution of the title compound from Step C (0.52 g, 2.78 mmol) in CH2Cl2 (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 h. Water (1 mL) was added. The mixture was extracted with CH2Cl2 (3×10 mL), and dried over Na2SO4. The solvent was removed. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (3/7) to give the title compound as a colorless gum. 1H NMR (CDCl3, 500 MHz) δ 4.76 (d, J=4.5 Hz, 1H), 3.88 (m, 1H), 2.61 (s, 3H), 2.59 (s, 3H).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×10 mL)
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed
  4. customThe residue was purified by column chromatography on silica gel Biotage 40S
  5. washeluting with EtOAc/hexane (3/7)

Sources & evidence

ORD record
ord-08eca4cccf484be1b2c13e24f3d3bbb3
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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