Sodium Chloride → HCID 90413489, compound

HRID 1746056Notes

Reaction equation

HRID 1746056 reaction equation
Br[C:2]1[C:12]([Cl:13])=[CH:11][C:5]2[O:6][C:7]([F:10])([F:9])[O:8][C:4]=2[CH:3]=1.[Cl-].[Li+].C([Mg+])(C)C.[Cl-].C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C.[NH4+].[Cl-].[Na+].[Cl-]>O1CCCC1.C(OCC)(=O)C>[Cl:13][C:12]1[C:2]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)=[CH:3][C:4]2[O:8][C:7]([F:10])([F:9])[O:6][C:5]=2[CH:11]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 115436085-Bromo-6-chloro-2,2-difluorobenzo[d][1,3]dioxoleHCID 178461732HCID 178461732, compound

Product 1

HCID 90413489HCID 90413489, compoundYield 101.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

5-Bromo-6-chloro-2,2-difluorobenzo[d][1,3]dioxole (1.0 g, 3.7 mmol) was dissolved in dry tetrahydrofuran (7 mL), cooled to 0-5° C. and treated in portions with isopropylmagnesium lithium chloride (1.3 M; 3.0 mL, 3.9 mmol). After 30 min, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (730 mg, 4.0 mmol) was added, and stirring was continued for 45 min at 10-15° C. Saturated NH4Cl (10 mL) was added and the mixture was shaken with ethyl acetate (20 mL) and saturated NaCl (10 mL). The organic phase was washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (1.2 g, qt): 1H NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.53 (s, 1H), 1.30 (s, 12H); 19F NMR (376 MHz, DMSO-d6) δ −48.97 (s); EIMS m/z 318.

Workup

  1. waitwas continued for 45 min at 10-15° C
  2. washThe organic phase was washed with saturated NaCl (10 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1be1ce62e9ce4087b50c2722f4a51234
Source dataset
uspto-grants-2015_10
Patent number
US09149038B2

Reaction notes

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