Hydrochloric Acid → HCID 66693659, compound

HRID 1469181Notes

Reaction equation

HRID 1469181 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)[CH:3]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 66692858HCID 66692858, compound

Product 1

HCID 66693659HCID 66693659, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of bromide 10 (9.7 g, 32.6 mmol) in CH2Cl2 (100 mL) was added boron tribromide (40 mL, 39.2 mmol, 1M in CH2Cl2) dropwise at 0° C. The mixture was warmed up to room temperature slowly and stirred at room temperature for 3 hours. To the mixture was added aq. 1N HCl solution (200 mL) dropwise at 0° C. The mixture was extracted with CH2Cl2 (150 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the desired product 12 (5.64 g, 61%).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (150 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-78a6e71fcaa24c05be4c25d184599a44
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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