6-Bromonaphthalene-2-carbaldehyde → HCID 59270578, compound

HRID 446216Notes

Reaction equation

HRID 446216 reaction equation
[C:1]1([N:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[Si](C)(C)C)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[Br:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[CH:43]=[C:42]([CH:47]=O)[CH:41]=[CH:40]2>O1CCCC1>[Br:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[CH:43]=[C:42](/[CH:47]=[C:14](/[C:11]1[CH:10]=[CH:9][C:8]([N:7]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:13][CH:12]=1)\[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:41]=[CH:40]2

Participants

5

Reactant 3

HCID 134770296-Bromonaphthalene-2-carbaldehydeHCID 59270598HCID 59270598, compoundHCID 178418339Butyllithium

Product 1

HCID 59270578HCID 59270578, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N,N-diphenyl-4-(phenyl(trimethylsilyl)methyl) aniline (5.0 g, 12.3 mmol) was dissolved in purified tetrahydrofuran (30 mL) under a nitrogen atmosphere, and n-butyllithium (8.4 mL, 13.5 mmol) was slowly added thereto at −78° C. The reaction mixture solution was stirred at room temperature for 8 hours. 6-bromo-2-naphthaldehyde (2.9 g, 12.3 mmol) dissolved in tetrahydrofuran (10 mL) was added thereto at room temperature. The reaction mixture solution was stirred at room temperature for 24 hours. The reaction mixture solution was subjected to extraction with dichloromethane and distilled water, and the extracted material is subjected to column chromatography (hexane:dichloromethane=9:1). The reaction solvent was removed, and then the residue material was dried in vacuum to thereby obtain a pale yellow solid (4.5 g, yield: 66%).

Workup

  1. customat −78° C
  2. additionwas added
  3. customat room temperature
  4. stirringThe reaction mixture solution was stirred at room temperature for 24 hours
  5. extractionThe reaction mixture solution was subjected to extraction with dichloromethane
  6. distillationdistilled water
  7. customThe reaction solvent was removed
  8. customthe residue material was dried in vacuum

Sources & evidence

ORD record
ord-ec16f921da3f43a18227a08c17d1c9ea
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

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