(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 69583773, compound

HRID 860574Notes

Reaction equation

HRID 860574 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][CH:5]=[C:6]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:14]=[CH:13]4)[CH:7]=2)[O:2]1.C1OC2C=CC(B(O)O)=CC=2O1.[Br-:37].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:37][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:14]=[CH:13]3)[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12

Participants

5

Reactant 3

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 21124087Pyridiniumtribromide2×HCID 69583708HCID 69583708, compound

Product 1

HCID 69583773HCID 69583773, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 6-[4,5-methylenedioxyphenyl]-2-naphthoate (19.61 g, 56.50 mmol, prepared in a similar manner via a Suzuki coupling of 3,4-methylenedioxyphenyl boronic acid and 6-carboethoxynaphthyl-2-trifluoromethanesulfonate, 84% yield) in CH2Cl2 (900 mL) was pyridinium tribromide (19.91 g, 62.26 mmol) at RT. The resulting mixture was allowed to stir overnight. After 24 hours, additional amount of pyridinium tribromide (9.05 g, 28.3 mmol) was added and the mixture stirred overnight. The mixture was washed with H2O, brine and dried over magnesium sulfate. After filtering, the solvent was removed and purified on silica gel (CH2Cl2) to give ethyl 6-[3-bromo-4,5-methylenedioxyphenyl]-2-naphthoate (100%) as a white solid. 1H NMR (300 MHz; CDCl3): δ 1.47 (t, J=7.2 Hz, 3H), 4.46 (q, J=7.2 Hz, 2H), 6.05 (s, 2H), 6.90 (s, 1H), 7.15 (s, 1H), 7.57 (dd, J1=9.0 Hz, J2=1.5 Hz, 1H), 7.84 (s, 1H), 7.90 (d, J=9.0 Hz, 1H), 7.98 (d, J=9.0 Hz, 1H), 8.64 (s, 1H).

Workup

  1. customat RT
  2. waitAfter 24 hours
  3. stirringthe mixture stirred overnight
  4. washThe mixture was washed with H2O, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtering
  7. customthe solvent was removed
  8. custompurified on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-e152dbc501604207b6fa3298b7eacab9
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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