Acetic Acid → 2-Acetoxy-3-bromo-tetrahydropyran

HRID 49579Notes

Reaction equation

HRID 49579 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.[C:15]([OH:18])(=[O:17])[CH3:16]>C(OCC)C>[C:15]([O:18][CH:14]1[CH:13]([Br:8])[CH2:12][CH2:11][CH2:10][O:9]1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80803,4-dihydro-2H-pyranHCID 67184N-bromobutanimide

Product 1

HCID 122985732-Acetoxy-3-bromo-tetrahydropyranYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the solution of N-bromosuccimide (4.5 g ) in acetic acid (14.5 ml), was added dropwise 2.3 ml of 3,4-dihydro-2H-pyran at 10° C. The reaction mixture was diluted with 50 ml of diethyl ether and washed with 50 ml of water three times. The organic layer was washed with 1N NaHCO3 solution, dried, and then concentrated under a reduced pressure to give 4.1 g of 2-acetoxy-3-bromo-tetrahydropyran as a colorless oil (yield: 73%).

Workup

  1. washwashed with 50 ml of water three times
  2. washThe organic layer was washed with 1N NaHCO3 solution
  3. customdried
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-e8b7fdd7e15b4edca43e03658d05f9d4
Source dataset
uspto-grants-2004_03
Patent number
US06706888B2

Reaction notes

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