Toluene → 6-(Benzyloxy)-3,4-dihydronaphthalen-2-ylboronic acid

HRID 709915Notes

Reaction equation

HRID 709915 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14](Br)[CH2:15][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.O1CCCC1.C([Li])(C)(C)C.CCCCC.[B:42](OC(C)C)([O:47]C(C)C)[O:43]C(C)C>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12](=[CH:11][CH:10]=1)[CH:13]=[C:14]([B:42]([OH:47])[OH:43])[CH2:15][CH2:16]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 1140TolueneHCID 8003PentaneHCID 8028TetrahydrofuranHCID 21531Triisopropyl borateHCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthaleneHCID 178418306HCID 178418306, compound

Product 1

HCID 674100386-(Benzyloxy)-3,4-dihydronaphthalen-2-ylboronic acid

Procedure

7-Benzyloxy-3-bromo-1,2-dihydro-naphthalene (21.75 g, 0.06900 mol) was azeotroped with toluene (100 mL, 0.9 mol) and dried on the high vacuum for 30 min. This was dissolved in tetrahydrofuran (200 mL, 2 mol), cooled with a dry ice-isopropanol bath under an atmosphere of nitrogen. 1.70 M tert-Butyllithium in pentane (89.3 mL, 0.152 mol) was added slowly, stirred for 10 min. Triisopropyl borate (79.1 mL, 0.345 mol) was added and the mixture was stirred for 1 hour with cooling then brought to r.t. The reaction was quenched with ice-water. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered, concentrated and dried on the high vacuum to give a crude intermediate, 6-(benzyloxy)-3,4-dihydronaphthalen-2-ylboronic acid.

Workup

  1. customdried on the high vacuum for 30 min
  2. temperaturecooled with a dry ice-isopropanol bath under an atmosphere of nitrogen
  3. stirringthe mixture was stirred for 1 hour
  4. temperaturewith cooling
  5. customthen brought to r.t
  6. customThe reaction was quenched with ice-water
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  9. washThe combined organic layers were washed with water, brine
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customdried on the high vacuum

Sources & evidence

ORD record
ord-8855ba9723994a5ba35655f7aa9374ce
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

Loading…