Hydrochloric Acid → (4-{[tert-Butyl(diphenyl)silyl]oxy}-3-methoxyphenyl)boronic acid

HRID 1375220Notes

Reaction equation

HRID 1375220 reaction equation
[Li]CCCC.Br[C:7]1[CH:30]=[CH:29][C:10]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([O:31][CH3:32])[CH:8]=1.C([O:36][B:37](OC(C)C)[O:38]C(C)C)(C)C.Cl>C1COCC1>[C:25]([Si:12]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[O:11][C:10]1[CH:29]=[CH:30][C:7]([B:37]([OH:38])[OH:36])=[CH:8][C:9]=1[O:31][CH3:32])([CH3:27])([CH3:28])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 10863116(4-Bromo-2-methoxy-phenoxy)-tert-butyl-diphenyl-silaneHCID 178418339Butyllithium

Product 1

HCID 21079851(4-{[tert-Butyl(diphenyl)silyl]oxy}-3-methoxyphenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., 140 ml n-BuLi (1.6 M in hexane, 223.8 mmol) in 600 ml THF are added to a solution of 89.92 g (203.4 mmol) (4-bromo-2-methoxy-phenoxy)-tert-butyl-diphenyl-silane over a period of 30 minutes. After further 30 minutes at −78° C., 140.9 ml (610.4 mmol) triisopropylborate are added over a period of 30 minutes. The mixture is allowed to warm up to room temperature and is then hydrolysed at 0° C. with a 10% HCl solution within 30 minutes. After separation of the water phase, the organic phase is dried over MgSO4, condensed and the residue is crystallized-from ethyl acetate and a mixture of ethyl acetate/heptane, yielding. 4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-phenyl-boronic acid is isolated as a light yellow solid (m.p. 193–196° C.).

Workup

  1. customAfter separation of the water phase
  2. dry with materialthe organic phase is dried over MgSO4, condensed
  3. additiona mixture of ethyl acetate/heptane
  4. customyielding

Sources & evidence

ORD record
ord-52c42fff1da64202b48815e5090788f7
Source dataset
uspto-grants-2007_01
Patent number
US07166746B2

Reaction notes

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