Bromine → HCID 67374784, compound

HRID 1517549Notes

Reaction equation

HRID 1517549 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([OH:8])=[O:7].CC([O-])=O.[Na+].[Br:21]Br>CC(O)=O>[Br:21][C:9]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]([O:2][CH3:1])=[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:10]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 127397584-tert-Butyl-3-methoxybenzoic acid

Product 1

HCID 67374784HCID 67374784, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

step 1—To a solution of 3-methoxy-4-tert-butylbenzoic acid (1.0 eq, 48.02 mmol, 10.00 g and NaOAc (2.0 eq, 96.03 mmol, 7.88 g) in HOAc (75 mL) at RT was added dropwise Br2 (2.0 eq, 96.03 mmol, 4.94 mL). The resulting mixture was heated at 50° C. for 24 h, cooled to RT and poured into a mixture of ice-water. The slightly orange-colored solid was collected by suction filtration, washed with water, dried in the oven at 40° C. to afford 12.87 g of 6-bromo-4-tert-butyl-3-methoxybenzoic acid the product (118).

Workup

  1. temperaturecooled to RT
  2. filtrationThe slightly orange-colored solid was collected by suction filtration
  3. washwashed with water
  4. customdried in the oven at 40° C.

Sources & evidence

ORD record
ord-b87c6be46afa4d1b82056429a0d9c82e
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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