Hexamethylphosphoramide → 1-(3-Bromo-2-methylphenoxy)tricyclo[3.3.1.13,7]decane

HRID 588666Notes

Reaction equation

HRID 588666 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2.CN(C)P(N(C)C)(N(C)C)=O>C(OCC)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2

Participants

5

Reactant 3

HCID 12679HexamethylphosphoramideHCID 791061-BromoadamantaneHCID 111714303-Bromo-2-methylphenol

Product 1

HCID 866812631-(3-Bromo-2-methylphenoxy)tricyclo[3.3.1.13,7]decane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

3-Bromo-2-methylphenol (1000 mg) and 1-bromoadamantane (2013 mg) were added to hexamethylphosphoramide (8 mL) and the mixture was heated in a microwave reactor (Biotage) at 250° C. for 35 minutes. The solution was taken up in diethyl ether, washed with water two times, washed with brine, dried on anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by flash column chromatography on silica gel using 2% ethyl acetate (hexanes) increasing to 5% ethyl acetate (hexanes) to yield the title compound.

Workup

  1. washwashed with water two times
  2. washwashed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography on silica gel using 2% ethyl acetate (hexanes)
  7. temperatureincreasing to 5% ethyl acetate (hexanes)

Sources & evidence

ORD record
ord-db2c60b7b0b6461f9a5163dca4f7fa90
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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