Sodium Carbonate → 5-Bromo-6-(4-fluorophenyl)-1,3-benzodioxole

HRID 1598844Notes

Reaction equation

HRID 1598844 reaction equation
Br[C:2]1[C:10]([Br:11])=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:11][C:10]1[C:2]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)=[CH:3][C:4]2[O:8][CH2:7][O:6][C:5]=2[CH:9]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2258145,6-Dibromo-1,3-dioxaindaneHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 234510685-Bromo-6-(4-fluorophenyl)-1,3-benzodioxoleYield 71.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Under nitrogen, 1.1 g of Pd(PPh3)4 was added to a stirred solution of 10.4 g (37.2 mmol) of 5,6-dibromo-1,3-benzodioxole and 2.6 g (18.6 mmol) of 4-fluorophenylboronic acid in 100 mL of toluene, 60 mL of ethanol, and 40 mL of M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2 SO4. Purification by silica gel chromatography (Waters Prep-500A) with hexane as the eluent gave 3.9 g (71%) of 5-bromo-6 (4-fluorophenyl)-1,3-benzodioxole as a colorless solid: mp 86.0°-87.5° C.; NMR (CDCl3) δ 6.02 (s, H), 6.77 (s, 1H), 7.04-7.13 (m, 3H), 7.28-7.35 (m, 2H).

Workup

  1. temperatureat reflux overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried over Na2 SO4
  6. customPurification by silica gel chromatography (Waters Prep-500A) with hexane as the eluent

Sources & evidence

ORD record
ord-e319f95d97134e2aa2a0a61c339112c3
Source dataset
uspto-grants-1998_04
Patent number
US05739166

Reaction notes

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