Carbon tetrabromide → HCID 14797061, compound

HRID 1925768Notes

Reaction equation

HRID 1925768 reaction equation
[CH2:1](OC1CCCCO1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14].C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:23][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1167412H-Pyran, tetrahydro-2-(11-tetradecyn-1-yloxy)-

Product 1

HCID 14797061HCID 14797061, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alkynyl ether 16 (5.62 g, 0.0191 mol) in dichloromethane (150 ml) at 0° C. was treated successively with carbon tetrabromide (8.23 g, 0.0248 mol) and triphenylphosphine (13 g, 0.050 mol) and stirred for 5 h at r.t. The solution was treated with silica gel, the solvent removed invacuo and the dry residue loaded onto a prepared flash column. Elution with hexanes yielded the pure bromide 17 (87% from 15); δH (270 MHz, CDCl3) 1.10 (3H, t, J 7.4), 1.27-1.54 (14H, m), 1.84 (2H, quin, J 7.3), 2.15 (4H, m) and 3.40 (2H, t, J 6.8). δC (100 MHz, CDCl3) 12.82, 14.79, 27.28, 29.23, 29.26, 29.4, 29.53, 29.80, 29.80, 30.11, 33.04, 79.96 (quartenary) and 82.00 (quartenary).

Workup

  1. additionThe solution was treated with silica gel
  2. customthe solvent removed invacuo
  3. washElution with hexanes

Sources & evidence

ORD record
ord-a94a35e108b445198fb8d593f1f131d6
Source dataset
uspto-grants-2012_05
Patent number
US08178713B2

Reaction notes

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