Water → HCID 57995575, compound

HRID 385315Notes

Reaction equation

HRID 385315 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Br:18]Br.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Br:18][C:7]1[CH:6]=[C:5]([CH:8]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24408BromineHCID 58150495HCID 58150495, compound

Product 1

HCID 57995575HCID 57995575, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of ethyl 2-(4-hydroxyphenyl)-4-methylpentanoate E-9 (15 g, 63.55 mmol) in 100 ml of glacial acetic acid at 0° C., slowly added bromine (20.26 g, 64.14 mol) and stirred at same temperature for 2.5 h. After completion the reaction, the reaction mixture was poured into water and neutralized with saturated sodium carbonate solution and extracted with ethyl acetate (300 ml×3). The organic layer was washed with water, saturated sodium bicarbonate solution and brine. The organic layer was then distilled off to yield product ethyl 2-(3-bromo-4-hydroxyphenyl)-4-methylpentanoate. Yield: (16 g, 80%). 1H NMR (CDCl3): δ 7.20 (m 2H), 6.80 (d, J=7.9 Hz, 1H), 4.90 (bs, 1H), 4.15 (q, 2H), 3.60 (t, 1H), 1.95-2.00 (m, 1H), 1.75-1.80 (m, 1H), 1.45-1.50 (m, 1H), 1.20 (t, 3H), 1.00 (m, 6H). Mass: (315, M+1, 100%).

Workup

  1. customAfter completion the reaction
  2. extractionextracted with ethyl acetate (300 ml×3)
  3. washThe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  4. distillationThe organic layer was then distilled off

Sources & evidence

ORD record
ord-ab8bcd04c5924a7a9bb9a77725b1ce18
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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