Diethyl Ether → 2-(2-Bromophenyl)ethan-1-ol

HRID 1474281Notes

Reaction equation

HRID 1474281 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](O)=[O:10].[BH4-].[Na+].B(F)(F)F.CCOCC>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 877542-Bromophenylacetic acidHCID 4311764Sodium borohydride

Product 1

HCID 27340892-(2-Bromophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (2-bromophenyl)acetic acid (100 g, 0.46 mmol) in dry THF (2 L) was added NaBH4 (29 g, 0.77 mol) in portions. The contents were cooled to 0° C., and BF3. Et2O (123 mL, 0.770 mol) was added drop-wise over 1 h. The mixture was allowed to warm to 25° C. and stirred for 16 h. The reaction was cooled to 0° C. and cautiously quenched with aqueous sodium hydroxide. The contents were stirred for 3 h, and then extracted with EtOAc. The organic layer was dried and concentrated to give 2-(2-bromophenyl)ethanol. 1H-NMR (400 MHz, CDCl3) δ 7.54˜7.56 (m, 1H), 7.23˜7.28 (m, 2 H), 7.07˜7.11 (m, 1H), 3.88 (s, J=6.6 Hz, 2H), 3.03 (t, J=6.8 Hz, 2H).

Workup

  1. temperatureto warm to 25° C.
  2. temperatureThe reaction was cooled to 0° C.
  3. customcautiously quenched with aqueous sodium hydroxide
  4. stirringThe contents were stirred for 3 h
  5. extractionextracted with EtOAc
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2f7fc23ea88141edb562039802c736b3
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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