Boron tribromide → Methyl (3-chloro-5-hydroxyphenyl)acetate

HRID 656753Notes

Reaction equation

HRID 656753 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12]CC2C=CC=CC=2)[CH:6]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58372832HCID 58372832, compound

Product 1

HCID 58372721Methyl (3-chloro-5-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3-benzyloxy-5-chloro-phenyl)-acetic acid methyl ester (8 g, 28 mmol) in CH2Cl2 (100 mL) at 0° C. was added boron tribromide (1M in CH2Cl2; 56 mL, 56 mmol). The reaction mixture was warmed to room temperature over 30 minutes and stirred for 2 hours. Once no starting material was seen by analytical LCMS and tlc, the mixture was cooled to 0° C. and quenched with H2O (50 mL). The volume was reduced, and the residue was diluted with EtOAc (500 mL). The solid material was filtered, and the organic layer was separated and concentrated. The crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customquenched with H2O (50 mL)
  3. additionthe residue was diluted with EtOAc (500 mL)
  4. filtrationThe solid material was filtered
  5. customthe organic layer was separated
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-75b528a26a52431f90c34f9afbd71541
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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