Bromine → 4-(2-Bromo-5-methoxyphenyl)-3,3-dimethylbutanoic acid

HRID 1274163Notes

Reaction equation

HRID 1274163 reaction equation
[CH3:1][C:2]([CH3:16])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[CH2:3][C:4]([OH:6])=[O:5].[Br:17]Br>C(Cl)Cl>[Br:17][C:13]1[CH:12]=[CH:11][C:10]([O:14][CH3:15])=[CH:9][C:8]=1[CH2:7][C:2]([CH3:16])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 221204124-(3-Methoxyphenyl)-3,3-dimethylbutanoic acid

Product 1

HCID 221203984-(2-Bromo-5-methoxyphenyl)-3,3-dimethylbutanoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3,3-dimethyl-4-(3-methoxyphenyl)butanoic acid (6.7 g, 0.03 mol) in DCM (100 mL) at 0° C. was added a solution of bromine (1.55 mL, 0.03 mol) in DCM (13 mL) dropwise. After addition the solution was stirred at 0° C. for 1 h then the solution was washed with water (3×100 mL), dried (Na2SO4) and evaporated. The product (8.45 g, 94%) was isolated as a brown oil and used without further purification. 1H NMR (360 MHz, CDCl3) δ 1.12 (6H, s), 2.36 (2H, s), 2.98 (2H, s), 3.80 (3H, s), 6.65 (1H, dd, J=8.7 and 3.1 Hz), 6.85 (1H, d, J=3.1 Hz), 7.43 (1H, d, J=8.7 Hz).

Workup

  1. additionAfter addition the solution
  2. washthe solution was washed with water (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a5da5cf6f6bf4e81b3bcee7773200397
Source dataset
uspto-grants-2000_12
Patent number
US06156761

Reaction notes

Loading…