HCID 67078824, compound → HCID 89581362, compound

HRID 1501256Notes

Reaction equation

HRID 1501256 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9](O)=[O:10])=[CH:4][CH:3]=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67078824HCID 67078824, compound

Product 1

HCID 89581362HCID 89581362, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromophenyl)-2-phenoxyacetic acid (6 g, 19.6 mmol) in anhydrous tetrahydrofuran (100 mL) was added borane-tetrahydrofuran complex (1 M, 40 mL) at −5° C. The solution was stirred at room temperature for 15 hours. After 2 hours, LC-MS showed the desired product was obtained. Water:acetic acid (1:1, 50 mL) was added at 0° C. to quench the reaction, the mixture was added 10 mL saturated sodium bicarbonate to adjust pH=7, extracted with ethyl acetate (100 mL). Then combined and concentrated the organic layers. The crude product was purified by column chromatography (silica gel, dichloromethane/menthol=40:1) to give 2-(4-bromophenyl)-2-phenoxyethanol (5 g, 80%). LCMS (M+H+) m/z: calcd 292.06. found 292.

Workup

  1. waitAfter 2 hours

Sources & evidence

ORD record
ord-b24d3bfa3eb1448a928e2980d55fcf5c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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