Methanol → 1,4-Dibromo-2-methoxybenzene

HRID 2384928Notes

Reaction equation

HRID 2384928 reaction equation
C[C:2](C)([O-:4])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=1F.CO>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=1[O:4][CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 1370041,4-Dibromo-2-fluorobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 133995571,4-Dibromo-2-methoxybenzeneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Add dropwise potassium tert-butoxide (118.2 ml, 118.2 mmol, 1 M in hexane) to a solution of 1,4-dibromo-2-fluorobenzene (25.0 g, 98.5 mmol) in THF (492 mL) and MeOH (40 mL, 984.7 mmol) at RT. Heat the mixture at 70° C. overnight. Quench the mixture with water (50 mL), dilute with Et2O (400 mL), wash once with saturated NH4Cl (300 mL) and back extract the aqueous with Et2O (200 mL). Dry the combined organic phase over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph, eluting with 5-10% ethylacetate/hexane to give 22.0 g (84%) of the title compound. GC m/z (79Br81Br) 266 [M]+.

Workup

  1. customQuench the mixture with water (50 mL)
  2. additiondilute with Et2O (400 mL)
  3. washwash once with saturated NH4Cl (300 mL)
  4. extractionback extract the aqueous with Et2O (200 mL)
  5. dry with materialDry the combined organic phase over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude material by flash chromatograph
  9. washeluting with 5-10% ethylacetate/hexane

Sources & evidence

ORD record
ord-4859eb24b11242a09b20888a638cf701
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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