Hexane → 2-(2-Bromoethyl)naphthalene

HRID 236413

Reaction equation

HRID 236413 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33]N1C(=O)CCC1=O.CCCCCC>C1C=CC=CC=1>[Br:33][CH2:12][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 738772-Naphthaleneethanol

Product 1

HCID 2282702-(2-Bromoethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 25 g (145 mmole) of 2-(2-naphthyl)ethanol and 67.9 g (259 mmole) of triphenylphosphine in 200 ml of benzene was added in portions 46.1 g (259 mmole) of N-bromosuccinimide. A temperature of 45°-50° was maintained by cooling the reaction mixture as needed in an ice bath. After the mixture was poured into 750 ml of hexane and filtered, the filtrate was diluted with an additional 400 ml of hexane and allowed to stand overnight. The solution was concentrated to dryness and the resultant solid was purified by chromatography on silica gel. The title compound (30.5 g), m.p. 55°-57°, was homogeneous by thin-layer chromatography (5%, 10%, and 15% by volume ethyl acetate-hexane on silica gel plates), and was used in subsequent reactions without further purification.

Workup

  1. temperatureA temperature of 45°-50° was maintained
  2. temperatureby cooling the reaction mixture
  3. customas needed in an ice bath
  4. filtrationfiltered
  5. additionthe filtrate was diluted with an additional 400 ml of hexane
  6. concentrationThe solution was concentrated to dryness
  7. customthe resultant solid was purified by chromatography on silica gel
  8. customwas used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-46b89368cfbf462aace282a276fc3a70
Source dataset
uspto-grants-1987_02
Patent number
US04644071

Linked notes

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