1-Adamantanecarboxylic acid → 3-Bromoadamantane-1-carboxylic acid

HRID 561364

Reaction equation

HRID 561364 reaction equation
[C:1]12([C:11]([OH:13])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Al+3].[Cl-].[Cl-].[Cl-].[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][C:3]12[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][C:1]([C:11]([OH:13])=[O:12])([CH2:8]3)[CH2:2]1)[CH2:4]2

Participants

5

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 308183-Bromoadamantane-1-carboxylic acidYield 75.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

More specifically, adamantane-1-carboxylic acid (1) (45 g, 0.25 mol) was added to mixture of AlCl3 (45 g, 0.34 mol) and Br2 (450 g) at 0° C. and stirred at 0-10° C. for 48 hrs, kept 5 hrs at about 20° C., poured on to 500 g crushed ice, diluted with 300 ml CHCl3 and decolorized with solid Na2S2O5. The aqueous phase was extracted with Et2O (50 ml×2). The combined organic solution was washed with H2O and extracted with 10% NaOH. The alkaline extraction was acidified with 2N H2SO4 and provided 49 g (yield=75.7%) of 3-bromo-adamantane-1-carboxylic acid (2).

Workup

  1. waitkept 5 hrs at about 20° C.
  2. additionpoured on to 500 g
  3. customcrushed ice
  4. extractionThe aqueous phase was extracted with Et2O (50 ml×2)
  5. washThe combined organic solution was washed with H2O
  6. extractionextracted with 10% NaOH
  7. extractionThe alkaline extraction

Sources & evidence

ORD record
ord-6b59caeed860473ebe138cc2d2332a95
Source dataset
uspto-grants-2011_11
Patent number
US08063248B2

Linked notes

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