Hydrogen Bromide → 2,6-Dibromo-4-cholesten-3-one

HRID 866516Notes

Reaction equation

HRID 866516 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[BrH:29].[Br:30]Br>C(O)(=O)C.CCOCC>[Br:29][CH:19]1[CH2:20][C@@:21]2([CH3:22])[C:16]([CH:15]([Br:30])[CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:26]2([CH3:27])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])=[CH:17][C:18]1=[O:28]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 91477Cholest-4-en-3-one

Product 1

HCID 537421292,6-Dibromo-4-cholesten-3-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

60 g. of 4-cholesten-3-one is dissolved in 2 l. of ether and 1 ml. of hydrobromic acid in acetic acid, 37% strength. It is combined, with agitation, with a solution of 52.4 g. of bromine in 300 ml. of acetic acid. The mixture is then further stirred for 15 minutes, thereafter diluted with a small quantity of ether, and washed in succession with water, sodium bicarbonate solution, and water. After drying and evaporation, 90 g. of crude 2,6-dibromo-4-cholesten-3-one is obtained in the form of an oil.

Workup

  1. washwashed in succession with water, sodium bicarbonate solution, and water
  2. customAfter drying
  3. customevaporation, 90 g

Sources & evidence

ORD record
ord-1797bca2b0ed4f2dbb4114f574d36893
Source dataset
uspto-grants-1978_07
Patent number
US04100026

Reaction notes

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