1-Bromo-3-chloropropane → HCID 21181453, compound

HRID 2399827Notes

Reaction equation

HRID 2399827 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[F:10][C:11]([F:25])([F:24])[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH:21]([CH3:23])[CH3:22])[C:19]#[N:20])=[CH:14][CH:13]=1.Br[CH2:27][CH2:28][CH2:29][Cl:30]>C1(C)C=CC=CC=1.O1CCCC1>[F:10][C:11]([F:24])([F:25])[C:12]1[CH:13]=[CH:14][C:15]([C:18]([CH:21]([CH3:23])[CH3:22])([CH2:27][CH2:28][CH2:29][Cl:30])[C:19]#[N:20])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 3280088Npc316347HCID 21181229HCID 21181229, compound

Product 1

HCID 21181453HCID 21181453, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution consisting of a 0.5M solution of bis(trimethylsilyl)amide in toluene (2.2 mL, (1.1 mmoles) and tetrahydrofuran (7.8 mL) stirring at -78° under an argon atmosphere was added dropwise a solution of the compound of Example 7, Step (a) (227 g, 1.00 mmole) in tetrahydrofuran (1.0 mL). After stirring for 1.0 hour at -78°, 3-bromo-1-chloropropane (236 mg 1.50 mmoles) was added in one portion, and the resulting mixture was stirred for 30 minutes at -78° and then 2.0 hours at room temperature. The mixture was partitioned between diethyl ether and water, the aqueous layer was extracted with ether, and the combined organic extracts were washed with water and then brine. After drying over sodium sulfate, the solution was filtered and then evaporated. A compound (271 mg) was obtained as a red oil which was characterized by NMR as follows: 1H NMR(CDCl3) d 7.65 (d, 2H), 7.53 (d, 2H), 3.48 (m, 2H), 1.19 (d, 3H), 0.79 (d, 3H).

Workup

  1. stirringAfter stirring for 1.0 hour at -78°
  2. stirringthe resulting mixture was stirred for 30 minutes at -78°
  3. custom2.0 hours
  4. customat room temperature
  5. customThe mixture was partitioned between diethyl ether and water
  6. extractionthe aqueous layer was extracted with ether
  7. washthe combined organic extracts were washed with water
  8. dry with materialAfter drying over sodium sulfate
  9. filtrationthe solution was filtered
  10. customevaporated

Sources & evidence

ORD record
ord-dc0901f13d49400082dc955aff5ea373
Source dataset
uspto-grants-1995_09
Patent number
US05451604

Reaction notes

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