HCID 10082161, compound → HCID 19855477, compound

HRID 898883Notes

Reaction equation

HRID 898883 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14](=[O:16])[CH3:15])[CH2:7][CH2:6]2.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14](=[O:16])[CH3:15])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 10082161HCID 10082161, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 19855477HCID 19855477, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a suspension of N-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (1.57 g; 7.2 mmol) in CH2Cl2 (70 mL), cooled to −60° C., is added a solution of boron tribromide-CH2Cl2 (36 mL), dropwise to maintain the reaction temperature between −50 to −60° C. The gelatinous suspension is allowed to warm to RT and stir for 30 min. The reaction is cooled to 0° C., quenched with satd NaHCO3 and stirred for 30 min at RT. The mixture is extracted with CH2Cl2 (2×), the extracts combined, dried over Na2SO4, filtered and evaporated under reduced pressure to provide a crude solid, which was purified by flash chromatography (SiO2) eluting with a CH2Cl2-MeOH gradient to afford 1.13 g (76%) of N-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide as a beige solid.

Workup

  1. temperaturedropwise to maintain the reaction temperature between −50 to −60° C
  2. temperatureto warm to RT
  3. temperatureThe reaction is cooled to 0° C.
  4. customquenched with satd NaHCO3
  5. stirringstirred for 30 min at RT
  6. extractionThe mixture is extracted with CH2Cl2 (2×)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto provide a crude solid, which
  11. customwas purified by flash chromatography (SiO2)
  12. washeluting with a CH2Cl2-MeOH gradient

Sources & evidence

ORD record
ord-6d744c7dea9c45f684c3bc61c3b8294a
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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