Benzyl Bromide → HCID 58292737, compound

HRID 1798112Notes

Reaction equation

HRID 1798112 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292737HCID 58292737, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 0.8 mmol) in anhydrous DMF (3 mL) was added sodium hydride (0.08 g, 1.6 mmol). After stirring for 15 minutes bromomethyl-benzene (0.274 g, 1.6 mmol) was added and the resulting mixture stirred at room temperature for 4 hours then quenched with crushed ice. The pH was adjusted to 4 with 6M HCl and the mixture extracted with EtOAc. The organic extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by Biotage (5-60% EtOAc in hexane) to give 6-benzyloxy-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 73%). 1H NMR 400 MHz (DMSO-d6) δ 9.15 (s, 1H), 7.45-7.31 (m, 5H), 7.11 (d, J=2.0 Hz, 1H), 6.94 (d, =2.0 Hz, 1H), 5.44 (dd, J=9.2, 2.4 Hz, 1H), 5.10 (s, 2H), 4.05 (q, J=7.2 Hz, 2H), 3.08 (dd, J=15.2, 2.4 Hz, 1H), 2.26 (s, 3H), 2.21 (m, 1H), 1.08 (t, 3H).

Workup

  1. additionwas added
  2. customthen quenched with crushed ice
  3. extractionthe mixture extracted with EtOAc
  4. washThe organic extracts were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by Biotage (5-60% EtOAc in hexane)
  9. customto give 6-benzyloxy-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 73%)

Sources & evidence

ORD record
ord-a432fb7b496a41afb554f1a476f74f06
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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