Adamantanone → Tert-butyl 3-chloro-4-(2-hydroxyadamantan-2-yl)benzoate

HRID 1849788Notes

Reaction equation

HRID 1849788 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.Br[C:13]1[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][C:14]=1[Cl:26].[Cl-].[Li+].C([Mg]Cl)(C)C>O1CCCC1>[Cl:26][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][C:13]=1[C:2]1([OH:11])[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)[C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 64151AdamantanoneHCID 81295241Tert-butyl 4-bromo-3-chlorobenzoateHCID 178461733HCID 178461733, compound

Product 1

HCID 86703670Tert-butyl 3-chloro-4-(2-hydroxyadamantan-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−40° C.) solution of 2-adamantanone (1.50 g, 10.00 mmol) and tert-butyl 4-bromo-3-chlorobenzoate (2.45 g, 10.00 mmol) in anhydrous tetrahydrofuran (120 mL) was added isopropylmagnesium chloride lithium chloride complex (1.3 M solution in tetrahydrofuran, 10 mL, 13 mmol). The reaction mixture was warm to ambient temperature over 2 hours and heated to reflux for 1 hour. After cooling to ambient temperature, the mixture was quenched with saturated aqueous ammonium chloride (10 mL), diluted with ethyl acetate (200 mL), washed with saturated aqueous ammonium chloride

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling to ambient temperature
  4. customthe mixture was quenched with saturated aqueous ammonium chloride (10 mL)
  5. additiondiluted with ethyl acetate (200 mL)
  6. washwashed with saturated aqueous ammonium chloride

Sources & evidence

ORD record
ord-7f85903e6c0b4ea7a9034bd089732c5a
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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