Triphenylphosphine → (Z)-1-Bromo-4-decene

HRID 1943Notes

Reaction equation

HRID 1943 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.O1CCCCC1O[CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(Cl)Cl>[Br:20][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 67591886(4Z)-1-(tetrahydropyran-2-yloxy)-4-decene

Product 1

HCID 10932932(Z)-1-Bromo-4-deceneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cool solution of triphenylphosphine (0.72 g, 2.74 mmol) and bromine (0.41 g, 2.6 mmol) in CH2Cl2, a solution of (4Z)-1-(tetrahydropyran-2-yloxy)-4-decene (16) (0.41 g, 1.71 mmol), prepared according to Example 16, in methylene chloride was added dropwise. Isolation and purification by conventional means afforded the product 17 in 90% yield (0.33 g). 1H NMR (200 MHz ) δ: 5.42 (dtt, J=11.0, 7.0, 7.0, 1.0, 1.0 Hz, 2H, CH=CH-4, 5); 3.41 (t, J=6.6, 6.6 Hz, 2H CH2 -1, 2.20 (dt, J=7.0, 7.0 Hz, 2H, CH2 -3); 2.04 (dr, J=6.5, 6.5 Hz, 2H, CH2 -6); 1.91 (tt, J=6.5, 6.5, 6.5 Hz, 2H, CH2 -2); 1.30 (m, 6H, CH2 -7, 8, 9); 0.89 (t, J=7.0 Hz, CH3). MS [EI, m/z(%)] 220 (M+ -8), 218 (M+, 8), 164 (12), 162 (12), 150 (23), 148 (23), 135 (8), 109 (12), 97 (44), 95 (14), 83 (55), 82 (14), 81 (37), 79 (15), 70 (21), 69 (100), 67 (39), 56 (29), 55 (93), 54 (20), 43 (21), 42 (20), 41 (92), 39 (30). IR (CCl4, cm-1) 3008 (cis CH=CH), 1246 (RCH2CH2Br), 649, 566 (C--Br).

Workup

  1. additionwas added dropwise
  2. customIsolation and purification by conventional means

Sources & evidence

ORD record
ord-486cc915e99745379d961e1fc7268a73
Source dataset
uspto-grants-1998_03
Patent number
US05728376

Reaction notes

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