Boron tribromide → 4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

HRID 272805Notes

Reaction equation

HRID 272805 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:19]#[N:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:19]#[N:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9751334-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrileYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M in DCM, 262 ml) was added to a solution of 4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonitrile (14.7 g, 67.9 mmol) in DCM (294 ml) at 0° C. under N2 keeping the temperature below 5° C. The reaction was allowed to warm to room temperature and stirred for 48 hours. The mixture was cooled to −10-0° C. with dry ice acetone and quenched with saturated aqueous sodium bicarbonate (294 ml). The mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was separated and the aqueous extracted with DCM (3×250 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give the title compound (10.8 g, 78%).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate (294 ml)
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 hour
  4. customThe mixture was separated
  5. extractionthe aqueous extracted with DCM (3×250 ml)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. washwashed with DCM
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b19e594fff174b419899a7f02c5986e6
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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