1,4-Dibromobutane → HCID 12510312, compound

HRID 259366Notes

Reaction equation

HRID 259366 reaction equation
[C:1]12([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([F:19])[CH:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[CH2:21][CH2:22][CH2:23][CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>C(O)C>[C:1]12([O:11][C:12]3[CH:18]=[CH:17][C:15]([N:16]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[C:14]([F:19])[CH:13]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 12510278HCID 12510278, compound

Product 1

HCID 12510312HCID 12510312, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.3 g (8.8 mmoles) of 4-(1-adamantyloxy)-2-fluoroaniline, 1.90 g (8.80 mmoles) of 1,4-dibromobutane, and 2.68 g (19.4 mmoles) of K2CO3 in deaerated absolute ethanol (25 ml) is refluxed for twenty-four hours. The solvent is evaporated, and the residue taken up in methylene chloride (125 ml) and water (125 ml). The methylene chloride layer is washed with 2×125 ml of water, and the combined aqueous portions are extracted with methylene chloride (50 ml). The combined methylene chloride layers are dried and concentrated. The crude product is chromatographed by high pressure liquid chromatography on a 2.54 × 109 cm column at approximately 40 psi, eluting with 0.5% acetone in methylene chloride and collecting 200 ml fractions. Fraction 3 contains 1.5 g of tan solid, m.p. 99.0°-105.9° C.

Workup

  1. temperatureis refluxed for twenty-four hours
  2. customThe solvent is evaporated
  3. washThe methylene chloride layer is washed with 2×125 ml of water
  4. extractionthe combined aqueous portions are extracted with methylene chloride (50 ml)
  5. dry with materialThe combined methylene chloride layers are dried
  6. concentrationconcentrated
  7. customThe crude product is chromatographed by high pressure liquid chromatography on a 2.54 × 109 cm column at approximately 40 psi
  8. washeluting with 0.5% acetone in methylene chloride
  9. customcollecting 200 ml fractions

Sources & evidence

ORD record
ord-ed537221bbe44adfae37c05565fbd8b1
Source dataset
uspto-grants-1977_07
Patent number
US04036977

Reaction notes

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