Boron tribromide → HCID 178444417, compound

HRID 980425Notes

Reaction equation

HRID 980425 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:15]=2[F:22])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].B(Br)(Br)Br>ClCCl>[F:22][C:15]1[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=1[CH2:13][CH2:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178444419HCID 178444419, compound2×

Product 1

HCID 178444417HCID 178444417, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the 2-(trans-4-pentylcyclohexyl)-1-(2-fluoro-4-methoxyphenyl)-ethane (9.0 g, 0.0294 mol) obtained according to section (c) in absolute dichloromethane (100 ml) was added dropwise to a solution of boron tribromide (11.0 g, 0.0441 mol) and absolute dichloromethane (100 ml) under virtually anhydrous conditions at 0° C. The mixture thus formed was stirred for 1 hour and then poured onto ice water. The organic phase was separated off, and the aqueous phase was extracted again with dichloromethane (2×50 ml). The combined organic phases were washed with water and dried over magnesium sulfate. The crude product obtained after evaporation was recrystallized from hexane at 0° C. 8.5 g (98% yield) of pure target product were obtained.

Workup

  1. customThe mixture thus formed
  2. additionpoured onto ice water
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was extracted again with dichloromethane (2×50 ml)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe crude product obtained
  8. customafter evaporation
  9. customwas recrystallized from hexane at 0° C

Sources & evidence

ORD record
ord-075fe26bcdc64c0faa4a91e40b983119
Source dataset
uspto-grants-1987_01
Patent number
US04637897

Reaction notes

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