2-Bromobenzoic acid → HCID 14858794, compound

HRID 2081950Notes

Reaction equation

HRID 2081950 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)=O.CC(C)=O.[CH2:18]([Li])[CH2:19][CH2:20][CH3:21].[Cl-].[NH4+:24].[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[NH2:24][C:19]1[CH:20]=[CH:21][C:27]([CH2:28][CH:29]([C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[OH:25])=[CH:26][CH:18]=1

Participants

6

Reactant 5

HCID 69402-Bromobenzoic acidHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 14858794HCID 14858794, compound

Procedure

In another preparation, 2-bromobenzoic acid (957 mg, 4.8 mmol) was dissolved in 20 ml of tetrahydrofuran and cooled to -78° degrees C. (CO2 /acetone), n-butyl lithium (n-BuLi; 5.8 mM, 1.6M in hexanes, 9.2 mmol) was added nd stirred for one hour. Aldehyde Compound VI, (1.9 g, 3.2 mmol) dissolved in 10 ml tetrahydrofuran cooled to -78° degrees C. was added Via cannula, and thereafter stirred for four hours at -78° degrees C. The reaction mixture was poured into saturated ammonium chloride followed by extraction with (2×50 ml) ethyl acetate. The combined organic extracts were dried with sodium sulfate and purified by flash chromatography using neat methylene chloride yielding 860 mg, 62 percent of the theoretical amount. 1H NMR CDCl3) δ7.90-7.80 (m, 1H), 7.68-7.40 (m, 2H), 7.40-7.05 (m, 11H), 7.0 (d, J=8.6 Hz, 2H), 6.64 (d, J=8.6 Hz, 2H), 5.62 (t, J=7.1 Hz, 2H), 3.64 (br s, 2H), 3.4-2.8 (m, 2H).

Workup

  1. temperaturecooled to -78° degrees C
  2. temperaturecooled to -78° degrees C
  3. additionwas added Via cannula
  4. stirringstirred for four hours at -78° degrees C
  5. extractionfollowed by extraction with (2×50 ml) ethyl acetate
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9bacb758a3ae4e6c8f159c20e7f9bb81
Source dataset
uspto-grants-1993_02
Patent number
US05187086

Reaction notes

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