2-Bromotoluene → HCID 14858801, compound

HRID 2081952Notes

Reaction equation

HRID 2081952 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[C:6](=[O:8])=O.[CH3:9][C:10]([CH3:12])=O.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[Cl-].[NH4+:22]>C1COCC1>[NH2:22][C:18]1[CH:17]=[CH:16][C:15]([CH2:20][CH:6]([C:9]2[CH:5]=[CH:4][CH:3]=[CH:2][C:10]=2[CH3:12])[OH:8])=[CH:14][CH:19]=1

Participants

6

Reactant 4

HCID 72362-BromotolueneHCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 14858801HCID 14858801, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (2.8 ml, 2.6 M in hexanes, 4.4 mmol) was added to 30 ml THF and cooled to -78° degrees C. (CO2 /acetone). To this solution, 2-bromotoluene (0.573 ml, 4.8 mmol) was added and allowed to stir 30 minutes. Aldehyde Compound VI, (1.9 g, 3.2 mmol) dissolved in 15 ml of THF and cooled to -78° degrees C. was next added, and the resulting mixture stirred for two hours. The reaction mixture was poured into a saturated ammonium chloride solution and extracted 2×25 ml with methylene chloride. The combined organic layers were dried with sodium sulfate and purified by flash chromatography in 6:1:1.5 hexanes:methylene chloride:ethyl acetate yielding 900 mg of Compound XII, 69 percent of the theoretical amount. 1H NMR (CDCl3) δ7.9-7.8 (m, 1H), 7.68-7.40 (m, 2H), 7.40-7.15 (m, 12H), 7.05 (d, J=8.6 Hz, 2H), 6.70 (d, J=8.6 Hz, 2H), 5.3 (t, J=7.1 Hz, 1H), 4.62 (s, 4H) 3,0-2.7 (m, 2H), 2.3 (s, 3H). Anal. Calcd. for C29H29NO: C, 85.50; H, 7.13; N, 3.44. Found C, 85.58; H, 7.08; N, 3.41.

Workup

  1. temperaturecooled to -78° degrees C
  2. temperaturecooled to -78° degrees C
  3. stirringthe resulting mixture stirred for two hours
  4. extractionextracted 2×25 ml with methylene chloride
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. custompurified by flash chromatography in 6:1:1.5 hexanes

Sources & evidence

ORD record
ord-65e3e79d7d204446865bffa2f2d59c4a
Source dataset
uspto-grants-1993_02
Patent number
US05187086

Reaction notes

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