Hydrogen Bromide → HCID 12282365, compound

HRID 277923Notes

Reaction equation

HRID 277923 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](C2C=CC=CC=2)(O)[C:7]([OH:9])=[O:8])=[CH:2]1.CC(=O)OCC.[BrH:23]>C(O)(=O)C>[Br:23][CH:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 2885133193-25-7

Product 1

HCID 12282365HCID 12282365, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The (thiophen-3-yl)mandelic acid (8.60 g, 54.4 mmol) was dissolved in 100 ml of 30% HBr in acetic acid. The solution was stirred for 18 hours at RT. The clear black solution was poured onto 2.5 L of ice water and immediately extracted with Et2O (4×400 ml). The ether was dried over Na2SO4 and treated with decolorizing carbon. The Et2O was evaporated and the residue was azeotroped with toluene to remove residual acetic acid. The crude solid product was recrystalized from hexanes to yield 9.07 g. (75.%). EA, MS(FD).

Workup

  1. extractionimmediately extracted with Et2O (4×400 ml)
  2. dry with materialThe ether was dried over Na2SO4
  3. additiontreated with decolorizing carbon
  4. customThe Et2O was evaporated
  5. customthe residue was azeotroped with toluene
  6. customto remove residual acetic acid
  7. customThe crude solid product was recrystalized from hexanes
  8. customto yield 9.07 g

Sources & evidence

ORD record
ord-7916020dd742433aa960464e2ae1dfdf
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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