Boron tribromide → 6-Chloro-2'-fluoro-4-iodobiphenyl-3-ol

HRID 1619695Notes

Reaction equation

HRID 1619695 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[C:10]([I:12])[C:9]([O:13]C)=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21]>ClCCl>[Cl:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[CH:8][C:9]([OH:13])=[C:10]([I:12])[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 580423152-Chloro-2'-fluoro-4-iodo-5-methoxybiphenyl

Product 1

HCID 580423466-Chloro-2'-fluoro-4-iodobiphenyl-3-olYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (251 mg, 2.61 mmol) was added to a solution of 2-chloro-2′-fluoro-4-iodo-5-methoxybiphenyl (Preparation 95, 671 mg, 1.85 mmol) in dichloromethane (4.7 mL) at −20° C. and the mixture allowed to warm slowly to room temperature for 18 hours. The reaction was quenched by addition of water (10.0 mL), before being diluted with dichloromethane (30 mL). The organic phase was separated and washed with water (3×5.0 mL), brine (5.0 mL), dried over MgSO4, filtered and evaporated to give a purple oil. Column chromatography purification on silica, eluting with 1:4 ethyl acetate:heptanes gave the title compound (610 mg, 94%) as a colourless oil.

Workup

  1. customThe reaction was quenched by addition of water (10.0 mL)
  2. additionbefore being diluted with dichloromethane (30 mL)
  3. customThe organic phase was separated
  4. washwashed with water (3×5.0 mL), brine (5.0 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a purple oil
  9. customColumn chromatography purification on silica
  10. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-7566a60786ce43b98753b3a12d84156d
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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