Water → HCID 15867527, compound

HRID 714028Notes

Reaction equation

HRID 714028 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:8]([CH2:20][CH2:21][CH3:22])=[C:9]([CH:17]=[CH:18][CH:19]=1)[C:10]([O:12]C(C)(C)C)=[O:11].O>C1(C)C=CC=CC=1>[OH:6][C:7]1[C:8]([CH2:20][CH2:21][CH3:22])=[C:9]([CH:17]=[CH:18][CH:19]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 89690143HCID 89690143, compound

Product 1

HCID 15867527HCID 15867527, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-25 °C

Procedure

Add boron tribromide (305.6 mL, 305.6 mmol) dropwise while maintaining the temperature below 0° C. to a solution of tert-butyl 3-methoxy-2-propyl-benzoate (61.2 g, 244 mmol) in toluene (428 mL) which has been cooled to −25° C. Stir at −5° C. for 3 h. Add water (100 mL) dropwise, raising the temperature to 7° C., and stir 30 min. Concentrate the mixture in vacuo and then suspend the semisolid in water (200 mL). Stir 1 h and filter the suspension through a glass frit. Wash the collected solid with water and dry the solid to yield the title compound (43.1 g, 98%). 1H NMR (300 MHz, CDCl3) δ 7.58 (d, J=8.0 Hz, 1H); 7.16 (t, J=8.0 Hz, 1H); 6.99 (d, J=7.7 Hz, 1H); 5.0 (bs, 2H); 2.98 (t, J=7.7 Hz, 2H), 1.64 (m, 2H); 1.02 (t, J=7.4 Hz, 3H).

Workup

  1. stirringstir 30 min
  2. concentrationConcentrate the mixture in vacuo
  3. stirringStir 1 h
  4. filtrationfilter the suspension through a glass frit
  5. washWash the collected solid with water
  6. customdry the solid

Sources & evidence

ORD record
ord-fdf76c5e82184a4da1db638160036a8e
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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