Hydrochloric Acid → 2-(2-Benzyloxy-5-chlorophenyl)cyclopentene-1-boronic Acid

HRID 1767210Notes

Reaction equation

HRID 1767210 reaction equation
C([Li])CCC.Br[C:7]1[CH2:11][CH2:10][CH2:9][C:8]=1[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[B:27](OC(C)C)([O:32]C(C)C)[O:28]C(C)C.Cl>O1CCCC1.CCOCC>[CH2:20]([O:19][C:13]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=1[C:8]1[CH2:9][CH2:10][CH2:11][C:7]=1[B:27]([OH:32])[OH:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 211129001-Bromo-2-(2-benzyloxy-5-chlorophenyl)cyclopenteneHCID 178418339Butyllithium

Product 1

HCID 211129122-(2-Benzyloxy-5-chlorophenyl)cyclopentene-1-boronic AcidYield 58%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (0.73 ml, 1.6M in hexanes, 1.17 mmol) was added to a solution of 1-bromo-2-(2-benzyloxy-5-chlorophenyl)cyclopentene (424 mg, 1.17 mmol) in anhydrous tetrahydrofuran (12 ml) at −78° C. under nitrogen. The resulting solution was stirred for 15 minutes and triisopropyl borate (440 mg, 2.34 mmol) was added. The mixture was allowed to warm to room temperature, 1M hydrochloric acid (20 ml) was added and stirred vigorously for 15 minutes. After diluting with ether the organic phase was dried (magnesium sulphate), evaporated and purified by chromatography on silica (1:4 ethyl acetate/iso-hexane) to give the title compound as a white solid (214 mg, 58%). LC/MS: Rt 3.4, [2 MH−] 637.3.

Workup

  1. stirringstirred vigorously for 15 minutes
  2. dry with materialwas dried (magnesium sulphate)
  3. customevaporated
  4. custompurified by chromatography on silica (1:4 ethyl acetate/iso-hexane)

Sources & evidence

ORD record
ord-42cf77559e0e4c269ab81e6672b945c7
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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