Hydrochloric Acid → HCID 124019698, compound

HRID 718355Notes

Reaction equation

HRID 718355 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([B:26]2[O:30]C(C)(C)C(C)(C)[O:27]2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].Cl>CC(C)=O.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([B:26]([OH:30])[OH:27])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 123643209HCID 123643209, compound

Product 1

HCID 124019698HCID 124019698, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3,4-bis(3-methoxyphenethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (40 mg, 0.079 mmol) in Acetone (5 mL)/Water (2.500 mL) was added sodium periodate (50.9 mg, 0.238 mmol) and ammonium acetate (18.34 mg, 0.238 mmol) and the resulting mixture was stirred at room temp for 16 h. Then, 1N HCl (1 mL) was added and the mixture was stirred for 1 h. The mixture was diluted with EtOAc (10 mL) and washed with brine (5 mL), dried (Na2SO4), filtered and concentrated to afford (3,4-bis(3-methoxyphenethoxy)phenyl)boronic acid (29 mg, 0.069 mmol, 87% yield) as white solid. 1H NMR (400 MHz, CDCl3)) δ 7.82 (dd, J=8.0, 1.3 Hz, 1H), 7.69 (d, J=1.3 Hz, 1H), 7.28-7.22 (m, 2H), 7.02 (s, 1H), 6.96-6.90 (m, 4H), 6.85-6.77 (m, 2H), 4.31 (q, J=7.3 Hz, 4H), 3.83 (s, 3H), 3.80 (s, 3H), 3.17 (dt, J=14.0, 7.2 Hz, 4H).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. washwashed with brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f1830ecccfa45ccb1b5839034910d88
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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