Potassium Bromide → Methyl 3'-bromo-4'-methoxy-2-methylbiphenyl-4-carboxylate

HRID 2093138Notes

Reaction equation

HRID 2093138 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])=[CH:5][CH:4]=1.OOS([O-])=O.[K+].[K+].[Br-:27]>C(#N)C.O>[Br:27][C:8]1[CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 253877Potassium BromideHCID 23707502Potassium hydroxy sulfiteHCID 67065985Methyl 4-(4-methoxyphenyl)-3-methylbenzoate

Product 1

HCID 67066022Methyl 3'-bromo-4'-methoxy-2-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 4′-methoxy-2-methylbiphenyl-4-carboxylate (71.5 g, 0.279 mol) in acetonitrile (1.43 L) and water (572 mL) was added oxone (180.1 g, 0.293 mol). Then a solution of KBr (38.2 g, 0.321 mol) in water (143 mL) was slowly added over 30 minutes. The reaction was stirred for 2.5 hours, then water (715 mL) was added and the mixture was left standing for 1 hour. The solids were filtered and washed as follows: with a solution of MeCN/water (1:1, 350 mL, twice), water (700 mL, twice, then 350 mL) and dried to afford methyl 3′-bromo-4′-methoxy-2-methylbiphenyl-4-carboxylate. 1H NMR (CDCl3, 400 MHz) δ 7.94 (s, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.53 (d, J=2.2 Hz, 1H), 7.3-7.2 (m, 2H), 6.97 (d, J=8.4 Hz, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 2.32 (s, 3H).

Workup

  1. waitthe mixture was left
  2. waitstanding for 1 hour
  3. filtrationThe solids were filtered
  4. washwashed
  5. dry with materialwith a solution of MeCN/water (1:1, 350 mL, twice), water (700 mL, twice, then 350 mL) and dried

Sources & evidence

ORD record
ord-eccd44ba9b164891b8f5db6d3f6e7cc9
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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