Bromine → HCID 18399625, compound

HRID 381284Notes

Reaction equation

HRID 381284 reaction equation
[Br:1]Br.[C:3]([C:6]1[S:7][CH:8]=[C:9]([C:20]([O:22][CH3:23])=[O:21])[C:10]=1[O:11][C:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])(=[O:5])[CH3:4]>C(O)(=O)C>[Br:1][CH2:4][C:3]([C:6]1[S:7][CH:8]=[C:9]([C:20]([O:22][CH3:23])=[O:21])[C:10]=1[O:11][C:12]([CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:13])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 18399619HCID 18399619, compound

Product 1

HCID 18399625HCID 18399625, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 0.70 mL of bromine in 3.45 mL of acetic acid was added dropwise over a period of 60 minutes to a solution of 3.56 g of Compound 3A in 34.5 mL of acetic acid at 20-25° C. while stirring. After stirring further for 2.5 hours at 20-25° C., the mixture was poured into ice water and extracted with diethyl ether (2×80 mL). The combined organic layers were washed with water (2×80 mL), 10% aqueous sodium carbonate (100 mL) and water (3×80 mL), dried over sodium sulphate and evaporated to dryness in vacuo. The crude product was purified by flash chromatography in n-hexane/chloroform (6:4) to yield 1.31 g (29%) of Compound 3B.

Workup

  1. stirringAfter stirring further for 2.5 hours at 20-25° C.
  2. extractionextracted with diethyl ether (2×80 mL)
  3. washThe combined organic layers were washed with water (2×80 mL), 10% aqueous sodium carbonate (100 mL) and water (3×80 mL)
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness in vacuo
  6. customThe crude product was purified by flash chromatography in n-hexane/chloroform (6:4)

Sources & evidence

ORD record
ord-62a10996ca3c4eac969c78b2d34e4647
Source dataset
uspto-grants-2001_10
Patent number
US06306861B1

Reaction notes

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