Hydrochloric Acid → 3,3-Diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde

HRID 532218Notes

Reaction equation

HRID 532218 reaction equation
[CH2:1]([C:3]1([CH2:14][CH3:15])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:4]1=2)[CH3:2].C(OOC(=O)C1C=CC=CC=1)(=[O:23])C1C=CC=CC=1.C1C(=O)N(Br)C(=O)C1.C([O-])([O-])=O.[Na+].[Na+].Cl>C(Cl)(Cl)(Cl)Cl>[CH2:14]([C:3]1([CH2:1][CH3:2])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH:13]=[O:23])=[CH:12][C:4]1=2)[CH3:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7187Benzoyl PeroxideHCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 866850833,3-diethyl-5-methylbenzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 866850843,3-Diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehydeYield 561.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3,3-diethyl-5-methylbenzo[c][1,2]oxaborol-1(3H)-ol (2.0 g, 9.8 mmol) in CCl4 (25 ml) at rt was added benzoyl peroxide (237 mg, 0.98 mmol) followed by NBS (3.489 g, 19.6 mmol). The reaction mixture was refluxed for 16 h, cooled to rt and treated with aqueous Na2CO3. The aqueous layer was acidified with 3N HCl to pH=3 and extracted with EA (50 ml×3). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product (1.2 g, yield 56%) as white solid. 1H NMR (300 MHz, DMSO-d6): δ 10.06 (s, 1H), 9.30 (s, 1H), 7.85 (m, 3H), 1.86 (m, 4H), 0.55 (m, 6H). MS: m/z=219 [M+1]+.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. extractionextracted with EA (50 ml×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47be4f210347480484acee3b8895408e
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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