Bromine → HCID 87323401, compound

HRID 2425012Notes

Reaction equation

HRID 2425012 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:4].C([O-])(O)=O.[Na+]>CC(O)=O.C(Cl)(Cl)Cl>[CH2:3]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH2:16][Br:1])=[CH:11][C:10]=1[O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 67246495HCID 67246495, compound

Product 1

HCID 87323401HCID 87323401, compound

Reagents, catalysts & solvents 1

HCID 21584526Acetic acid chloroformSolvent2×

Procedure

Bromine (4.25 ml; 85 mmol) in AcOH:CHCl3 (1:1; 10 ml) was added to a vigorously stirred solution of the compound of example 20b (25.92 g; 80 mmol) in AcOH:CHCl3 (1:1; 110 ml) at 55-60° C. for 15 min. The mixture was stirred at room temperature for 5 min. and poured over crushed ice and NaHCO3 and extracted with EtOAc. The EtOAc layer was washed with water, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 3% CH3CN in chloroform) to obtain the title compound. Yield, 19.34 g, (60%); mp, 84-85° C. (EtOAc-PE 60-80° C.); analysis: C16H19O7Br: requires C, 47.66; H, 4.75; Br, 19.82. found: C, 48.08; H, 4.82; Br, 19.40%.

Workup

  1. additionpoured
  2. extractionextracted with EtOAc
  3. washThe EtOAc layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-c37faff01e7146b9b5e71063a20233a9
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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