Bromine → HCID 66823558, compound

HRID 1193213Notes

Reaction equation

HRID 1193213 reaction equation
[Br:1][C:2]1[CH:6]([CH3:7])[O:5][C:4]([CH3:9])([CH3:8])[C:3]=1[O:10]C(=O)C.BrBr>C(Cl)(Cl)Cl>[Br:1][CH:2]1[CH:6]([CH3:7])[O:5][C:4]([CH3:9])([CH3:8])[C:3]1=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 66823877HCID 66823877, compound

Product 1

HCID 66823558HCID 66823558, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of acetic acid 4-bromo-2,2,5-trimethyl-2,5-dihydrofuran-3-yl ester (19.14 g, 0.11 mol) (described in T. Hiyama et al. Bull. Chem. Soc. Jpn., 56, 3078-3087 (1983)) in anhydrous chloroform (75 ml) at −20° C. is added a solution of bromine (18.00 g, 0.11 mol) in anhydrous chloroform (200 ml) dropwise over 45 minutes. After stirring at this temperature for 30 minutes the reaction mixture was allowed to warm to room temperature, then further stirred for 1 hour. After dilution with chloroform (250 ml) the organic phase is washed with dilute aqueous sodium bicarbonate then brine, and the phases separated. Organics solvents are removed under reduced pressure to afford 4-bromo-2,2,5-trimethyldihydro-furan-3-one (23.50 g) as a dark orange oil. This material is used without purification in the next step.

Workup

  1. stirringfurther stirred for 1 hour
  2. washAfter dilution with chloroform (250 ml) the organic phase is washed with dilute aqueous sodium bicarbonate
  3. custombrine, and the phases separated
  4. customOrganics solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-2df8f3848cc945c1b205583c8439bfe7
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

Loading…