Carbon tetrabromide → HCID 18988272, compound

HRID 2396124Notes

Reaction equation

HRID 2396124 reaction equation
[CH2:1]([C:6]1[CH2:7][CH:8]([CH2:17]O)[S:9][CH2:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>C(Cl)Cl>[Br:39][CH2:17][CH:8]1[CH2:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][S:9]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18988213HCID 18988213, compound

Product 1

HCID 18988272HCID 18988272, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Part B. The alcohol from Part A above is dissolved in methylene chloride along with carbon tetrabromide, and cooled to 0° C. A methylene chloride solution of triphenylphosphine is added dropwise. The mixture is stirred for 14 hours, then evaporated and rapidly eluted through a plug ofsilica gel with an appropriate solvent system to afford 2-bromomethyl-3,6-dihydro-4,5-dipentyl-2H-thiopyran. This compound is useddirectly, and treated with potassium cyanide in dimethylsulfoxide at 80° C. until thin-layer chromatography shows the reaction is complete. At this point, the solution is cooled, and poured into 4 volumesof water. This mixture is extracted with ethyl acetate, and the extract is washed with more water (3× an equal volume), then brine, then dried over anhydrous magnesium sulfate, filtered and evaporated. Chromatography will then purify the product, (3,6-dihydro-4,5-dipentyl-2H-thiopyran-2-yl)acetonitrile.

Workup

  1. customevaporated
  2. washrapidly eluted through a plug ofsilica gel with an appropriate solvent system

Sources & evidence

ORD record
ord-bc2457747b0747d8a07e027338602a64
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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