Carbon Tetrachloride → HCID 67958735, compound

HRID 527641Notes

Reaction equation

HRID 527641 reaction equation
[CH3:1][C:2]1([CH3:22])[C:6]2[C:7]([O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[Br:23]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>C1COCC1>[Br:23][C:10]1[C:5]2[O:4][CH2:3][C:2]([CH3:1])([CH3:22])[C:6]=2[C:7]([O:11][Si:12]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:19]([CH3:21])[CH3:20])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimide2×HCID 67958526HCID 67958526, compound2×

Product 1

HCID 67958735HCID 67958735, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy][tris(1-methylethyl)]silane (Intermediate 181, 7.4 g, 23.19 mmol) was dissolved in THF (70.0 mL). N-Bromosuccinimide (4.2 g, 23.88 mmol) was added dissolving in few minutes. This mixture was stirred at room temperature for 3 hrs. More NBS (0.64 g, 3.48 mmol) was added and the reaction mixture was stirred at room temperature for a further hour. CCl4 (50 mL) was added to the reaction mixture and the solution was evaporated to dryness. The residue was re-suspended in CCl4 and stirred at room temperature for 15 min. The white solid was removed by filtration and the wet cake was washed with more CCl4. The CCl4 was swapped with ethyl acetate and the organic solution was washed three times with 2.5% w/w aqueous NaHCO3 and finally with water. The organic solution was dried on anhydrous Na2SO4 and evaporated to dryness to give the title compound (8.6 g) as a brown oil.

Workup

  1. dissolutiondissolving in few minutes
  2. stirringthe reaction mixture was stirred at room temperature for a further hour
  3. customthe solution was evaporated to dryness
  4. stirringstirred at room temperature for 15 min
  5. customThe white solid was removed by filtration
  6. washthe wet cake was washed with more CCl4
  7. washthe organic solution was washed three times with 2.5% w/w aqueous NaHCO3
  8. dry with materialThe organic solution was dried on anhydrous Na2SO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-005a8227072b4f30b166ed5f9ff60e13
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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