Hydrochloric Acid → [4-(Benzyloxy)-3-cyanophenyl]boric acid

HRID 1160808Notes

Reaction equation

HRID 1160808 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14](Br)=[CH:13][C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B:18]([O:27]C(C)C)([O:23]C(C)C)[O:19]C(C)C.C([Li])CCC.CCCCCC.Cl>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:19][B:18]([OH:27])[OH:23])=[CH:13][C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 22377852-(Benzyloxy)-5-bromobenzonitrileHCID 178418244HCID 178418244, compound

Product 1

HCID 66995522[4-(Benzyloxy)-3-cyanophenyl]boric acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(Benzyloxy)-5-bromobenzonitrile and triisopropyl borate were dissolved in a mixed solvent of THF and toluene, and at −78° C., an n-butyllithium/hexane solution was dropwise added. This was heated up to room temperature, and 1 M hydrochloric acid was added to the reaction mixture, followed by stirring to obtain [4-(benzyloxy)-3-cyanophenyl]boric acid. ES: 254.

Sources & evidence

ORD record
ord-a0163858732b4daaa60fd5a71fb90d47
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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