Carbon Tetrachloride → HCID 23501857, compound

HRID 1835594Notes

Reaction equation

HRID 1835594 reaction equation
C(Cl)(Cl)(Cl)Cl.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:28]N1C(=O)CCC1=O>ClCCl>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[C:17]([CH2:20][CH3:21])=[CH:18][C:19]=1[Br:28])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 23501791HCID 23501791, compound

Product 1

HCID 23501857HCID 23501857, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrachloride (30 mL) was used to dissolve 4-(Benzyloxy)-2-[(3-cyanopropyl)oxy]-1-ethylbenzene (2.5 g). N-bromosuccinimide (1.66 g) was added to the solution and it was stirred for 5.5 hours. The mixture was diluted with dichloromethane (50 mL), washed with water, dried over magnesium sulfate, filtered, and concentrated under vacuum. The resulting oil was crystallized from hexane/ethyl acetate at −20° C. to afford 1-(benzyloxy)-2-bromo-4-ethyl-5-[(3-cyanopropyl)oxy]-benzene as a white crystalline solid solution and it was stirred for 5.5 hours. The mixture was diluted with dichloromethane (50 mL), washed with water, dried over magnesium sulfate, filtered, and concentrated under vacuum. The resulting oil was crystallized from hexane/ethyl acetate at −20° C. to afford 1-(benzyloxy)-2-bromo-4-ethyl-5-[(3-cyanopropyl)oxy]-benzene as a white crystalline solid (1.5 g). NMR (CDCl3) 1.14, t (3H); 2.14, m (2H); 2.55, m (4H); 3.98, t (2H); 5.12, s (2H); 6.45, s (1H); 7.37, m (6H).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe resulting oil was crystallized from hexane/ethyl acetate at −20° C.

Sources & evidence

ORD record
ord-947eeb3a1811423a8b200dfa81674988
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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