Benzyl Bromide → 4-(3-Benzyloxycarbonyl-propoxy)-phenylboronic acid

HRID 735494Notes

Reaction equation

HRID 735494 reaction equation
[B:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)([OH:3])[OH:2].C(=O)(O)[O-].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([O:13][C:12]([CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([B:1]([OH:3])[OH:2])=[CH:16][CH:15]=1)=[O:14])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 57842761HCID 57842761, compound

Product 1

HCID 578426684-(3-Benzyloxycarbonyl-propoxy)-phenylboronic acidYield 30.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1A (200 mg, 0.89 mmol), potassium bicarbonate (313 mg, 3.1 mmol), and benzyl bromide (0.163 mL, 1.4 mmol) in DMF (2 mL) was heated at 60° C. for 8 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and hydrochloric acid (1 N). The aqueous layer was extracted with EtOAc (2×) and then the combined organics were washed with water (3×) and brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (30 to 100% EtOAc in hexane) to afford 1B (86 mg, 28%) as a white solid. 1H NMR (400 MHz, CD3OD) δ 2.08 (m, 2H), 2.56 (t, J=7.0 Hz, 2H), 4.00 (m, 2H), 5.12 (s, 2H), 6.84 (2×d, 2H), 7.32 (m, 5H), 7.7-7.5 (2×d, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and hydrochloric acid (1 N)
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washthe combined organics were washed with water (3×) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (30 to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-f6fb310c9ea64334b83ef662a4f1bcff
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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