Hydrochloric Acid → HCID 22723474, compound

HRID 1581867Notes

Reaction equation

HRID 1581867 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=2[CH:3]=1.C([Li])CCC.CN(C)[CH:43]=[O:44].Cl>O1CCCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:12]([C:11]3[CH:10]=[CH:9][C:8]([CH:43]=[O:44])=[CH:7][C:6]=3[C:5]2([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 36612112,7-Dibromo-9,9-didecylfluoreneHCID 178418339Butyllithium

Product 1

HCID 22723474HCID 22723474, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,7-dibromo-9,9-didecylfluorene (95.5 g, 0.158 mol) in terahydrofuran (THF, 375 mL), cooled In a dry-ice acetone bath, a 1.6 M solution of n-butyl lithium in hexanes (100 mL) was added over a period of 25 minutes. After stirring for 30 minutes a solution of dimethylforamide (DMF, 23 mL) in THF (25 ml) was added and the mixture was stirred for 1 hour in the cooling bath. After the mixture had been warmed to 0° C., hydrochloric acid (1:1, 50 mL) was added, diluted with toluene and the organic phase was separated, dried and concentrated. The residue that remained after rotary evaporation of the solvents was chromatographed over 600 g of silica gel. After elution with hexanes, the column was eluted with 1:3 toluene-hexane to obtain the aldehyde, 70.5 g, (81% yield), m.p. 45-47° C. A sample was recrystallized from a mixture of isopropanol and methanol, m.p. 49-49.5° C. IR (KBr; cm−1): 2922, 2853, 1696 (C═O), 1605, 1459. Anal. Calcd. for C34H49BrO: C, 73.76%; H, 8.92%; Br, 14.43%. Found: C, 73.75%; H, 8.86%; Br, 14.64%.

Workup

  1. additionwas added
  2. customthe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. customafter rotary evaporation of the solvents
  6. customwas chromatographed over 600 g of silica gel
  7. washAfter elution with hexanes
  8. washthe column was eluted with 1:3 toluene-hexane

Sources & evidence

ORD record
ord-48a462c74bd644159772831c92131eed
Source dataset
uspto-grants-2004_05
Patent number
US06730793B1

Reaction notes

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