Triphenylphosphine dibromide → 131665-74-2

HRID 1004642Notes

Reaction equation

HRID 1004642 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9]O.[Br:11]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:11][CH2:9][CH2:8][CH:2]1[CH2:3][CH:4]2[CH2:7][CH:1]1[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 35865672-Norbornaneethanol

Product 1

HCID 15752619131665-74-2Yield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bicylco[2.2.1]hept-2-yl-ethanol (13.0 g, 93 mmol) was dissolved in acetonitrile (200 mL) and treated with dibromotriphenylphosphorane (47.0 g, 0.11 mol). After 1.5 hours the mixture was quenched with water (10 mL), diluted with diethyl ether (400 mL), and washed with water (2×400 mL). The organic phase was dried (MgSO4) and concentrated to yield an oil. The product was passed through a pad of silica gel to yield 2-(2-bromo-ethyl)-bicyclo[2.2.1]heptane as a colorless oil (18 g, 95%). 1H NMR (CDCl3, 300 MHz) δ 3.37 (t, 7.4 Hz, 2 H), 2.22 (m, 1 H), 1.97 (m, 1 H), 1.86 (m, 1 H), 1.7-1.4 (m, 5 H), 1.3-0.9 (m, 5 H); MS (FAB) m/z 203 (MH+).

Workup

  1. customAfter 1.5 hours the mixture was quenched with water (10 mL)
  2. additiondiluted with diethyl ether (400 mL)
  3. washwashed with water (2×400 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customto yield an oil

Sources & evidence

ORD record
ord-0cdf78b201704951abb8156fcc6bbc87
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

Loading…