1,10-Dibromodecane → 1-Bromo-10-phenyldecane

HRID 405045Notes

Reaction equation

HRID 405045 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[Br:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2214831,10-DibromodecaneHCID 178506676HCID 178506676, compound

Product 1

HCID 27356021-Bromo-10-phenyldecaneYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 250 mL flask in ice-water bath was added 1,10-dibromodecane (46.0 g, 153 mmol) and anhydrous THF (100 ml) under nitrogen. Phenyl lithium (1.8 M in dibutyl ether, 28.5 mL, 51 mmol) was added dropwise. After addition was completed, the reaction mixture was stirred for 1 hour and warmed to room temperature. After 48 hours, it was quenched with H2O (200 mL), extracted with CH2Cl2 (200 mL×2) and dried. After concentration, the residue was distilled to give a colorless oil (9.35 g, yield 61.7%) at 130° C./0.07 mmHg. 1H NMR (CDCl3, 500 MHz) δ=7.27-7.32 (m, 2H), 7.20 (d, J=6.5 Hz, 3H), 3.43 (t, J=7.0 Hz, 2H), 2.62 (t, J=8.0 Hz, 2H), 1.84-1.96 (m, 2H), 1.60-1.68 (m, 2H), 1.41-1.52 (m, 2H), 1.24-1.41 (m, 10H).

Workup

  1. additionAfter addition
  2. waitAfter 48 hours
  3. customit was quenched with H2O (200 mL)
  4. extractionextracted with CH2Cl2 (200 mL×2)
  5. customdried
  6. concentrationAfter concentration
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-f3d2ba5383cc42e1b053521ffea6e486
Source dataset
uspto-grants-2014_06
Patent number
US08748739B2

Reaction notes

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