1,3-dihydro-1-hydroxy-3,3-dimethyl-2,1-benzoxaborole-6-carboxaldehyde synthesis

6synthesis methods

Product Name:1,3-dihydro-1-hydroxy-3,3-dimethyl-2,1-benzoxaborole-6-carboxaldehyde
CAS Number:1437051-71-2
Molecular formula:C10H11BO3
Molecular Weight:190

1,3-dihydro-1-hydroxy-3,3,6-trimethyl-2,1-benzoxaborole

1437051-62-1
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1,3-dihydro-1-hydroxy-3,3-dimethyl-2,1-benzoxaborole-6-carboxaldehyde

1437051-71-2
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Yield:1437051-71-2 65.4%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 20; for 16 h;Reflux;

Steps:

2.26b.6 Step 6:

Step 6:
Preparation of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde
To a solution of 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (6.87 g, 39 mmol) in CCl₄ (100 mL) at rt was added benzoyl peroxide (0.944 g, 3.9 mmol) followed by NBS (13.9 g, 78 mmol).
The reaction mixture was refluxed for 16 h, cooled to rt and treated with Na₂CO₃.
The aqueous layer was acidified with 3 N HCl to pH of 3 and extracted with EA.
The organic layer was washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure.
The residue was purified by column chromatography over silica gel eluted with DCM-MeOH (20:1) to give 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde (4.85 g; yield 65.4%) as a pale yellow solid. ¹H NMR (500 MHz, CDCl₃) δ 10.06 (s, 1H), 8.15 (s, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 1.58 (s, 6H) ppm. MS: m/z=191.1 (M+1, ESI+).