N-bromobutanimide → Ethyl 2-bromo-2-(2-naphthyl)acetate

HRID 989522Notes

Reaction equation

HRID 989522 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[Br:17]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:17][CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 256821Ethyl 2-naphthylacetate

Product 1

HCID 13438951Ethyl 2-bromo-2-(2-naphthyl)acetateYield 82%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution consisting of ethyl 2-(2-naphthyl)acetate (1.07 grams, 5.0 mmol), N-bromosuccinimide (0.89 grams, 5.0 mmol), benzoyl peroxide (0.05 grams), and carbon tetrachloride (50 mL) was heated at reflux until complete as determined by hplc (3 hours). The reaction was cooled to ambient temperature, washed with water (2×25 mL), dried using sodium sulfate, and filtered. The filtrate was concentrated to dryness. The residue was purified using a Biotage Flash 40M system eluting with hexane:ethyl acetate (49:1) to give 1.20 grams (82%) of ethyl 2-bromo-2-(2-naphthyl)acetate, mp 80-82° C. MS (FIA) m/z 293.0 [(M+H)+]. Anal. calcd. for C14H13O2Br: C, 57.36; H, 4.47. Found: C, 57.62; H, 4.54. 1H nmr (CDCl3): δ 1.27-1.33 (t, 3H), 4.18-4.36 (m, 2H), 5.56 (s, 1H), 7.52-7.55 (m, 2H), 7.71-7.76 (m, 1H), 7.82-7.92 (m, 3H), 7.97 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux until complete
  3. customas determined by hplc (3 hours)
  4. washwashed with water (2×25 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to dryness
  8. customThe residue was purified
  9. washeluting with hexane:ethyl acetate (49:1)

Sources & evidence

ORD record
ord-16b52cf786dc48b0a04357d2fa8f9cb6
Source dataset
uspto-grants-2003_10
Patent number
US06639076B1

Reaction notes

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