1-Bromodecane → HCID 19813937, compound

HRID 467337Notes

Reaction equation

HRID 467337 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C[O-].[Na+].[Na].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CO>[CH2:14]([S:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 81731-BromodecaneHCID 660494-BromothiophenolHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 19813937HCID 19813937, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Bromothiophenol (100 g) was added dropwise to a solution of sodium methoxide prepared from sodium (13.4 g) and dry methanol (400 ml). The solution was stirred for 1 hour and then a mixture of 1-bromodecane (128.6 g) and dry methanol (150 ml) was added over 10 minutes. The oily suspension was refluxed for 4 hours and was then concentrated by distilling off about 300 ml of solvent. Water (750 ml) was added and the mixture was stirred vigorously while cooling. The solid product was collected, washed with water and then crystallized from ethanol to give 4-(decylthio)bromobenzene (159.5 g), m.p. 37°-39° C. [Elemental analysis: C,58.0; H,7.7; Br,24.5; S,9.7%; calculated: C,58.36; H,7.60; Br,24.31; S,9.73%].

Workup

  1. additionwas added over 10 minutes
  2. temperatureThe oily suspension was refluxed for 4 hours
  3. concentrationwas then concentrated
  4. distillationby distilling off about 300 ml of solvent
  5. additionWater (750 ml) was added
  6. stirringthe mixture was stirred vigorously
  7. temperaturewhile cooling
  8. customThe solid product was collected
  9. washwashed with water
  10. customcrystallized from ethanol

Sources & evidence

ORD record
ord-7d77232fdc1d49c793b412d1e212595f
Source dataset
uspto-grants-1992_10
Patent number
US05159114

Reaction notes

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