Ethanol → (4-Bromomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

HRID 1798252Notes

Reaction equation

HRID 1798252 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:19]C3CCCCO3)[CH:14]=[C:15]([CH2:16]OC)[C:7]1=2)[CH3:2].B(Br)(Br)[Br:28].C(O)C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:19])[CH:14]=[C:15]([CH2:16][Br:28])[C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 58292743[1-Hydroxy-4-methoxymethyl-6-(tetrahydro-pyran-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

Product 1

HCID 58292861(4-Bromomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-hydroxy-4-methoxymethyl-6-(tetrahydro-pyran-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester from step 1.10. (870 mg, 1.37 mmol) in DCM (10 mL) was added boron tribromide (0.46 mL, 3.02 mmol) slowly under −78° C. The reaction mixture was allowed to stir at room temperature for 1 h. Ethanol was added slowly and the solvent was removed under vacuum. The crude product was used for next step without further purification. 1H NMR (300 MHz, CD3CN) δ 7.13 (s, 1H), 7.01 (s, 1H), 5.62 (dd, 1H), 4.42-4.63 (dd, 2H), 4.14 (q, 2H), 3.18-3.24 (dd, 1H), 2.40-2.51 (m, 1H), 1.22 (t, 3H).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe crude product was used for next step without further purification

Sources & evidence

ORD record
ord-e4ff86b0b3bc47f0a009eafec27f9c91
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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