Ammonium Chloride → HCID 67971948, compound

HRID 445115Notes

Reaction equation

HRID 445115 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>CO>[Br:17][C:18]1[CH:19]=[C:20]([CH2:21][NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 765833-Bromobenzaldehyde2×HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 67971948HCID 67971948, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.0 g) and 3-bromobenzaldehyde (0.93 g) were dissolved in methanol (15 mL) and to the resultant solution, sodium triacetoxyborohydride (1.2 g) was added, followed by stirring the resultant reaction mixture at room temperature for 2 hours. To the reaction mixture, 3-bromobenzaldehyde (0.17 g) and sodium triacetoxyborohydride (0.6 g) were further added, and the reaction mixture was stirred further for 1.5 hours. To the resultant reaction mixture, a saturated ammonium chloride aqueous solution was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate 30:1 to 10:1) to obtain the subject compound (0.67 g) as a colorless oil.

Workup

  1. additionwas added
  2. customreaction mixture at room temperature for 2 hours
  3. stirringthe reaction mixture was stirred further for 1.5 hours
  4. customTo the resultant reaction mixture
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with saturated saline
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  9. customthe resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate 30:1 to 10:1)

Sources & evidence

ORD record
ord-ee8a0cc24dc24b249765cba421a4d7e0
Source dataset
uspto-grants-2013_07
Patent number
US08476287B2

Reaction notes

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