Bromine → HCID 54567611, compound

HRID 363042Notes

Reaction equation

HRID 363042 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:19]Br>C(O)=O.CCOC(C)=O.[Fe]>[CH:1]1([CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[Br:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 24408BromineHCID 54475829HCID 54475829, compound

Product 1

HCID 54567611HCID 54567611, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 284Formic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 23-2 (26.3 g, 106 mmol) was warmed on a steam bath in 110 mL of HCOOH with 592 mg (10.6 mmol) of Fe powder. Bromine (7.6 mL, 147.4 mmol) in 50 mL of HCOOH was added by dropping funnel over a period of 10 min. The reaction mixture was stirred an additional 1 h , cooled and poured onto ice. The resulting gum was taken up in 500 mL of EtOAc and washed with sat'd Na2S2O3 (2×150 mL), water (5×100 mL), sat'd NaHCO3 (3×100 mL) and brine (50 mL), dried (MgSO4) and concentrated to afford product 23-3 as a white solid.

Workup

  1. customof 10 min
  2. temperaturecooled
  3. additionpoured onto ice
  4. washwashed with sat'd Na2S2O3 (2×150 mL), water (5×100 mL), sat'd NaHCO3 (3×100 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d542fae7d6f940ad9bdb3e147bf6246a
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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