Bromine → HCID 16100372, compound

HRID 1424579Notes

Reaction equation

HRID 1424579 reaction equation
BrBr.[Br-:3].[Al+3].[Br-:5].[Br-].[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[NH:17][C:18](=[O:20])[CH3:19])[CH2:14]2.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:3][C:11]12[CH2:16][CH:7]3[CH2:14][C:13]([Br:5])([CH2:15][CH:9]([CH:8]3[NH:17][C:18](=[O:20])[CH3:19])[CH2:10]1)[CH2:12]2

Participants

6

Reactant 4

HCID 24408BromineHCID 64498HCID 64498, compoundHCID 166749BromhydrolHCID 23665763Sodium Bisulfite

Product 1

HCID 16100372HCID 16100372, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To bromine (20 mL, 40 mmol) and aluminum bromide (3.2 g, 20 mmol) was added N-(2-adamantyl)acetamide (4 g, 20 mmol) in portions. The reaction mixture was heated to 90° C. and stirred overnight. The mixture was cooled to rt and poured into ice/water. Satd aq sodium bisulfite was added slowly followed by dilution with CH2Cl2. The organic layer was separated, washed with brine, dried, filtered and concentrated. The crude product was purified by column chromatography to afford N-(5,7-dibromo-2-adamantyl)acetamide (1.98 g, 28%).

Workup

  1. temperatureThe mixture was cooled to rt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a123b8d7cca5420693a43676e6190de1
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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