Hydrochloric Acid → {5'-Chloro-2'-[(phenylmethyl)oxy]-2-biphenylyl}boronic acid

HRID 269568Notes

Reaction equation

HRID 269568 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[B:28](OC(C)C)([O:33]C(C)C)[O:29]C(C)C.Cl>O1CCCC1>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[B:28]([OH:33])[OH:29])[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 693094132'-Bromo-5-chloro-2-[(phenylmethyl)oxy]biphenylHCID 178418339Butyllithium

Product 1

HCID 69312320{5'-Chloro-2'-[(phenylmethyl)oxy]-2-biphenylyl}boronic acidYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.6M butyllithium in hexanes (16.8 ml, 26.88 mmol) was added over 10 minutes to a stirred solution of 2′-bromo-5-chloro-2-[(phenylmethyl)oxy]biphenyl (9.29 g, 25.56 mmol) in tetrahydrofuran (120 ml) at −78° C. under nitrogen. After stirring for 15 minutes triisopropyl borate (9.61 g, 51.12 mmol) was added over 2 minutes and the mixture allowed to warm to room temperature. 2M hydrochloric acid (150 ml) was added with vigorous stirring for 25 minutes and the organic phase was separated, dried (magnesium sulphate) and evaporated. The residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:4) then triturated with iso-hexane to give 5.15 g of white solid.

Workup

  1. additionwas added over 2 minutes
  2. customthe organic phase was separated
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. customThe residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:4)
  6. customthen triturated with iso-hexane

Sources & evidence

ORD record
ord-f715cd8ce70d41af81c300bd444ef450
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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