1-Bromo-3-chloropropane → HCID 21181672, compound

HRID 1386519Notes

Reaction equation

HRID 1386519 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([CH:21]([CH3:23])[CH3:22])[C:19]#[N:20].Br[CH2:25][CH2:26][CH2:27][Cl:28]>O1CCCC1>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([CH:21]([CH3:23])[CH3:22])([CH2:25][CH2:26][CH2:27][Cl:28])[C:19]#[N:20]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 14245132HCID 14245132, compound

Product 1

HCID 21181672HCID 21181672, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of a 0.5 M solution of potassium bis(trimethylsilyl)amide (12.4 mL and tetrahydrofuran (44 mL) stirring at −78° under argon was added dropwise a solution of the title product of Example 8, Step (a) (1.00 g) in tetrahydrofuran (2 mL). After stirring at −78° for 0.5 hour, 1-bromo-3-chloropropane (1.3 g) was added, and the mixture was stirred while being permitted to warm to room temperature. The mixture was partitioned between diethyl ether and saturated aqueous ammonium chloride, the aqueous layer was extracted with two portions of ether, the combined organic extracts washed with brine, dried over magnesium sulfate, filtered and evaporated to give a compound (1.20 g) which was characterized by NMR, as follows: 1H NMR(CDCl3) d 7.64-7.00(m, 4H), 3.50(t, 2H), 1.24(d, 3H), 0.82(d, 3H).

Workup

  1. stirringAfter stirring at −78° for 0.5 hour
  2. stirringthe mixture was stirred
  3. customThe mixture was partitioned between diethyl ether and saturated aqueous ammonium chloride
  4. extractionthe aqueous layer was extracted with two portions of ether
  5. washthe combined organic extracts washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8bc8335cd18647238e509dfe56cda438
Source dataset
uspto-grants-2001_07
Patent number
US06265439B1

Reaction notes

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