Hydrochloric Acid → HCID 59297263, compound

HRID 2234740Notes

Reaction equation

HRID 2234740 reaction equation
[Br:1][C:2]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:17])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.C[C:19]([CH3:22])([O-])[CH3:20].[K+].Br[CH2:25][CH2:26][CH3:27].Cl>CO.O.CS(C)=O>[Br:1][C:2]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:17])=[CH:9][CH:10]=3)[C:5]([CH2:25][CH2:26][CH3:27])([CH2:20][CH2:19][CH3:22])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78401-Bromopropane2×HCID 23665647Potassium tert-butoxide2×HCID 59297265HCID 59297265, compound

Product 1

HCID 59297263HCID 59297263, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred mixture of 2,7-dibromo-3-methoxyfluorene (87.7 g, 0.244 mol), potassium t-butoxide (28 g, 0.25 mol) and dry methyl sulfoxide (500 mL) was added 1-bromopropane (22.6 mL, 0.25 mol) at such a rate as to keep the reaction exotherm temperature below 45° C. A further quantity of potassium t-butoxide (39.0 g; 0.35 mol) and 1-bromopropane (31.6 mL; 0.35 mol) were added. The resulting mixture was stirred at room temperature for 1 hour and treated with 50% methanol/water (500 mL). The purple color was discharged by addition of 6.0M hydrochloric acid (2.0 mL) and the mixture cooled at 0° C. for 1 hour. The crude product was collected and washed with 50% methanol/water (250 mL) and dried to yield crude product (106 g). Purification by extraction from neutral alumina (5 cm3) with hexane on an Ace-Kauffman column with hexane afforded 2,7-dibromo-9,9-dipropyl-3-methoxyfluorene (95 g; m. pt. 127-131.5° C.). Further purification by re-crystallization (2-propanol) gave pure product (84 g, yield 78%).

Workup

  1. customthe reaction exotherm temperature below 45° C
  2. temperaturethe mixture cooled at 0° C. for 1 hour
  3. customThe crude product was collected
  4. washwashed with 50% methanol/water (250 mL)
  5. customdried
  6. customto yield crude product (106 g)
  7. customPurification
  8. extractionby extraction from neutral alumina (5 cm3) with hexane on an Ace-Kauffman column with hexane

Sources & evidence

ORD record
ord-08f7fa05f85c4ea1829544d3506b7fcb
Source dataset
uspto-grants-2010_05
Patent number
US07713452B2

Reaction notes

Loading…