Bromine → HCID 18640895, compound

HRID 1031420Notes

Reaction equation

HRID 1031420 reaction equation
[CH:1]([N:4]([CH:26]([CH3:28])[CH3:27])[C:5]([C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[CH:19][C:18]([OH:25])=[CH:17][C:16]=1[CH2:15][CH2:14]3)=[O:6])([CH3:3])[CH3:2].[Br:29]Br>C(O)(=O)C>[CH:26]([N:4]([CH:1]([CH3:2])[CH3:3])[C:5]([C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[C:19]([Br:29])[C:18]([OH:25])=[CH:17][C:16]=1[CH2:15][CH2:14]3)=[O:6])([CH3:28])[CH3:27].[CH:26]([N:4]([CH:1]([CH3:2])[CH3:3])[C:5]([C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[CH:19][C:18]([OH:25])=[C:17]([Br:29])[C:16]=1[CH2:15][CH2:14]3)=[O:6])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 24408BromineHCID 18640900HCID 18640900, compound

Product 2

HCID 18640895HCID 18640895, compoundHCID 18640898HCID 18640898, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of N,N-diisopropyl estr-1,3,5(10)-triene-3-ol-17β-carboxamide (1.85 g, 4.82 mmol) in 185 ml of warm acetic acid was cooled to 20° C. and 4.48 ml (4.82 mmol) of a 1.08 M solution of bromine in acetic acid was added slowly. After stirring at ambient temperature for 5 min, the reaction mixture was poured into ice water and extracted twice with dichloromethane. The combined dichloromethane extracts were washed twice with water, dried over anhydrous MgSO4 and concentrated. Chromatography (silica gel, 2% followed by 5% ether in dichloromethane) afforded 0.39 g of N,N-diisopropyl-2-bromo-estr-1,3,5(10)-triene-3-ol-17β-carboxamide and 0.75 g of N,N-diisopropyl-4-bromo-estr-1,3,5(10)-triene-3-ol-17β-carboxamide.

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined dichloromethane extracts were washed twice with water
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-82e17a2e18ba4bbdbe59948f2f696182
Source dataset
uspto-grants-1990_09
Patent number
US04954446

Reaction notes

Loading…