Bromine → Ethyl 2-(3-bromo-4-hydroxyphenyl)acetate

HRID 385325Notes

Reaction equation

HRID 385325 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Br:14]Br>C(Cl)(Cl)(Cl)Cl>[Br:14][C:7]1[CH:6]=[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

HCID 18620106Ethyl 2-(3-bromo-4-hydroxyphenyl)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ethyl 2-(4-hydroxyphenyl)acetate (20 g, 0.11 mol) in 200 ml of CCl4, was slowly added bromine (18.8 g, 0.11 mol) dissolved in 10 ml of CCl4 at 0° C. for 30 min. The reaction mass was stirred for another 30 min at 0° C. After completion of the reaction, the mixture was poured onto crushed ice and extracted with DCM (×2). The combined organic layers were washed with water, and 10% sodium bi-sulfite solution, dried over Na2SO4, filtered and concentrated in vacuo to give ethyl 2-(3-bromo-4-hydroxyphenyl)acetate in 78% yield. (22.4 g). 1HNMR (CDCl3): 7.42 (s, 1H); 7.14 (d, 1H); 6.97 (d, 1H); 5.53 (bs, 1H); 4.13 (q, 2H); 3.52 (s, 2H); 1.16 (t, 3H).

Workup

  1. customAfter completion of the reaction
  2. additionthe mixture was poured
  3. customonto crushed ice
  4. extractionextracted with DCM (×2)
  5. washThe combined organic layers were washed with water, and 10% sodium bi-sulfite solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7037eeb2e9ff4ad6b72c7e44ad2091da
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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