Hydrochloric Acid → HCID 16655411, compound

HRID 2116092Notes

Reaction equation

HRID 2116092 reaction equation
C([O:4][C@@H:5]([CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[OH:16])[CH2:6][Br:7])(=O)C.Cl>CO>[Br:7][CH2:6][C@@H:5]([OH:4])[CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[OH:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68961582HCID 68961582, compound

Product 1

HCID 16655411HCID 16655411, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S)-2-bromo-1-(5-fluoro-2-hydroxybenzyl)ethyl acetate (3.57 g, 12.2 mmol) in methanol was added hydrogen chloride (1.0 M in diethylether, 49 ml) and the reaction mixture was allowed to stir at room temperature for 12 h. The solvent was removed in vacuo and purification by flash column chromatography (silica, ethyl acetate:hexanes 3:7) afforded 2.95 g (97%) of (S)-2-(3-bromo-2-hydroxy-propyl)-4-fluoro-phenol as a colorless oil. HRMS ESI m/e 246.9761 [M−H]+; Calc'd 246.9755. [α]D25=+8.2° (c 0.71% in methanol).

Workup

  1. customThe solvent was removed in vacuo and purification by flash column chromatography (silica, ethyl acetate:hexanes 3:7)

Sources & evidence

ORD record
ord-2e4973f348a843ad8fc448602b973d03
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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