N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chloride → HCID 71572009, compound

HRID 532199Notes

Reaction equation

HRID 532199 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]([F:13])([F:12])[F:11])=[CH2:9])[CH:5]=[C:4]([F:14])[C:3]=1[F:15].[OH:16][N:17]=[C:18](Cl)[C:19]1[CH:30]=[CH:29][C:22]2[B:23]([OH:28])[O:24][C:25]([CH3:27])([CH3:26])[C:21]=2[CH:20]=1>CN(C=O)C>[CH3:26][C:25]1([CH3:27])[O:24][B:23]([OH:28])[C:22]2[CH:29]=[CH:30][C:19]([C:18]3[CH2:9][C:8]([C:10]([F:12])([F:13])[F:11])([C:6]4[CH:7]=[C:2]([F:1])[C:3]([F:15])=[C:4]([F:14])[CH:5]=4)[O:16][N:17]=3)=[CH:20][C:21]1=2

Participants

4

Reactant 2

HCID 86685046N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chlorideHCID 866850701,2,3-Trifluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 71572009HCID 71572009, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,2,3-trifluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene in DMF were added TEA (0.86 g, 1.18 mL, 8.52 mmol, 3 eq) and N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chloride (545 mg, 2.27 mmol, 0.8 eq) at 0° C. The reaction mixture was stirred for 12 h at rt, poured into ice-water and extracted with EA. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica column and prep-HPLC to give 105 mg pure product. 1H NMR (400 MHz, DMSO-d6): δ 9.23 (s, 1H), 7.76-7.59 (m, 5H), 4.43 (d, J=18.4 Hz, 1H), 4.28 (d, J=18.4 Hz, 1H), 1.48 (s, 3H), 1.47 (s, 3H) ppm; HPLC purity: 99.6% at 254 nm; MS: m/z=430 (M+1, ESI+).

Workup

  1. extractionextracted with EA
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica column

Sources & evidence

ORD record
ord-5ce60580751a4496b6ddb27503a4f1e3
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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