Bromine → Ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate

HRID 385374Notes

Reaction equation

HRID 385374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Br:15]Br>C(Cl)(Cl)(Cl)Cl>[Br:15][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:3]=[C:2]([Cl:1])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetate

Product 1

HCID 57995583Ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetateYield 81.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of compound ethyl 2-(3-chloro-4-hydroxyphenyl)acetate (11 g, 51 mmol) in 200 ml of CCl4, was slowly added bromine (8.22 g, 51 mmol) as a solution CCl4 (100 ml) at 0° C. over a period of 30 min. The reaction mixture was stirred for a further 30 min at 0° C. Upon which the reaction mixture was poured onto crushed ice and extracted with DCM (2×100 mL). The combined organic layers were washed with water followed by 10% sodium bisulfite solution, dried over Na2SO4 filtered and evaporated under reduced pressure to give ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate (12.2 g) as a white solid in 80% yield. 1HNMR (CDCl3): 7.37 (s, 1H); 7.27 (s, 1H); 5.68 (bs, 1H); 4.16 (q, 2H); 3.48 (s, 2H); 1.29 (t, 3H).

Workup

  1. customat 0° C.
  2. customof 30 min
  3. additionUpon which the reaction mixture was poured
  4. customonto crushed ice
  5. extractionextracted with DCM (2×100 mL)
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1c1b602a83ba4b759dc06387862f4890
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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