Hydrochloric Acid → HCID 67404056, compound

HRID 468005Notes

Reaction equation

HRID 468005 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH3:12])([OH:11])[CH3:10].C([Li])CCC.C([O:21][B:22](OC(C)C)OC(C)C)(C)C.Cl>C1COCC1.CCOC(C)=O.O>[CH3:10][C:9]1([CH3:12])[O:11][B:22]([OH:21])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 11009731HCID 11009731, compoundHCID 178418339Butyllithium

Product 1

HCID 67404056HCID 67404056, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-bromophenyl)-2-methylpropan-2-ol (3.48 g, 15 mmol) in THF (100 mL) cooled to −78° C. was added n-butyllithium (15.2 mL, 2.5M in hexanes) in a dropwise fashion. The reaction was permitted to stir for 10 minutes, prior to the addition of triisopropylborate (10.5 mL, 45 mmol). The reaction was permitted to stir for 16 hours, gradually warming to room temperature. Aqueous hydrochloric acid (10 mL, 6M) was added, and the mixture stirred for 1 hour. The reaction was diluted with EtOAc (250 mL) and water (50 mL). The organic portion was washed with brine, dried over sodium sulfate, and evaporated. The resultant crude material was purified by silica gel chromatography to yield 3,3-Dimethyl-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol as a white semisolid product. 1H NMR (400 MHz, acetone) δ ppm 1.13 (s, 6H) 2.76 (s, 2H) 6.99-7.04 (m, 1H) 7.05-7.14 (m, 1H) 7.21-7.27 (m, 1H) 7.58-7.64 (m, 1H). Amount obtained: 830 mg, 31% yield.

Workup

  1. stirringto stir for 16 hours
  2. stirringthe mixture stirred for 1 hour
  3. washThe organic portion was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe resultant crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e0ec9079f3949e1bd642c12da388fe7
Source dataset
uspto-grants-2014_01
Patent number
US08623911B2

Reaction notes

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