Carbon tetrabromide → 3-(Tridec-1-ynyl)benzyl bromide

HRID 255998Notes

Reaction equation

HRID 255998 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36]O)#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(Br)(Br)(Br)[Br:42]>ClCCl>[C:20]([C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][Br:42])#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 136885073-(Tridec-1-ynyl)benzyl alcohol

Product 1

HCID 136885083-(Tridec-1-ynyl)benzyl bromideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenyl phosphine (1.5 g, 5.7 mmole) was added in small portions to a stirred solution of 3-(Tridec-1-ynyl)benzyl alcohol (1.34 g, 4.7 mmol, from example 34) and carbon tetrabromide (1.87 g, 5.7 mmole) in dichloromethane (20 ml) at 0° C., and the mixture was stirred for a further 3 hr at this temperature. After removing all the solvent under reduced pressure, n-hexane (20 ml) was added and the precipitate of triphenylphosphine oxide removed by filtration. Removal of the hexane under reduced pressure gave an oil which was distilled to give the desired product, (1.49 g, 91%) B.p. 170° C. at 0.05 mmHg., νmax 690, 790, 1210, 1460, 1480, 1600, 2220, 2850, 2920 cm-1, δ(CDCl3) 0.7 (3H, distorted t, terminal CH3), 1.2 (18H, m, alkylene chain), 2.16 (2H, t J=7 Hz, CH2 adjacent to acetylene), 4.15 (CH, s, benzylics), 7.06 (4H, m, aromatics).

Workup

  1. customAfter removing all the solvent under reduced pressure, n-hexane (20 ml)
  2. additionwas added
  3. customthe precipitate of triphenylphosphine oxide removed by filtration
  4. customRemoval of the hexane under reduced pressure
  5. customgave an oil which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-7d85ce9a1a3a4baebd37dd096aea4d08
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Reaction notes

Loading…