1,2-Dibromoethane → HCID 13688472, compound

HRID 255995Notes

Reaction equation

HRID 255995 reaction equation
[CH:1](/[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[Br:25][CH2:26][CH2:27]Br>C(C(C)=O)C(C)C>[Br:25][CH2:26][CH2:27][O:18][C:15]1[CH:14]=[CH:13][C:12](/[CH:1]=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 78391,2-Dibromoethane2×HCID 11430Potassium CarbonateHCID 13688470HCID 13688470, compound

Product 1

HCID 13688472HCID 13688472, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

4-[(Z)-1-Undecenyl]phenol, (2.30 g, 9.30 mmol) and anhydrous potassium carbonate, (1.93 g, 14.0 mmol) in methyl isobutyl ketone (100 ml) were stirred and treated with 1,2-dibromoethane, (5.27 g, 29 mmol). The mixture was refluxed for 24 h after which time a further aliquot of 1,2-dibromoethane, (5.27 g, 28 mmol) was added. The mixture was refluxed a further 24 h, then cooled and washed with water, (twice). The organic phase was dried, (MgSO4), and evaporated in vacuo to an oil. Purification by column chromatography on silica gel, eluting with n-hexane then dichloromethane gave 1.34 g (41%) of the title compound as a white crystalline solid mp 40°-1° C. νmax (mull) 1510, 1573 (weak) 1610 cm-1, δ (CDCl3) 0.86 (3H, distorted t, terminal CH3), 1.26 (14H, m, (CH2)7), 2.26 (2H, m, allylic CH2), 3.60 (2H, t, J 6 Hz, CH2Br), 4.26 (2H, t, J 6 Hz, OCH2) 5.56 (1H, d.t, Jd 12 Hz, Jt 7 Hz, =CH--alkyl), 6.32 (1H, d, J 12 Hz, ArCH=), 7.06 (4H, ABq, Δν 33 Hz, J 9 Hz, C6H4).

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed a further 24 h
  3. temperaturecooled
  4. washwashed with water
  5. dry with materialThe organic phase was dried, (MgSO4),
  6. customevaporated in vacuo to an oil
  7. customPurification by column chromatography on silica gel
  8. washeluting with n-hexane

Sources & evidence

ORD record
ord-3fbac5d0361341fb8630fa7461358861
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Reaction notes

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