Boron tribromide → 1-(4-Hydroxyphenyl)cyclohexane-1-carbonitrile

HRID 272860

Reaction equation

HRID 272860 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 986291-(4-Methoxyphenyl)cyclohexanecarbonitrile

Product 1

HCID 198585061-(4-Hydroxyphenyl)cyclohexane-1-carbonitrileYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-methoxyphenyl)cyclohexanecarbonitrile (2 g, 9.29 mmol) in DCM (40 mL) at 0° C. under N2 was added dropwise BBr3 (2.63 mL, 27.87 mmol). The reaction was allowed to warm to room temperature and stirred for 48 hours. The mixture was stirred for 3 hours at 0° C. and quenched with water (30 mL). The mixture was separated and the organic layer was washed with a saturated aqueous solution of NaHCO3 then water. The combined organic extracts were dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel eluting with DCM:acetone (97:3) to give the title compound (1.71 g, 91%).

Workup

  1. stirringThe mixture was stirred for 3 hours at 0° C.
  2. customquenched with water (30 mL)
  3. customThe mixture was separated
  4. washthe organic layer was washed with a saturated aqueous solution of NaHCO3
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography on silica gel eluting with DCM:acetone (97:3)

Sources & evidence

ORD record
ord-645e7e4544bb403d8197706a894d9e71
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Linked notes

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