2-Bromobenzoic acid → 2-Bromobenzyl alcohol

HRID 1284265Notes

Reaction equation

HRID 1284265 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[Br:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16].CCCCCC>O1CCCC1>[Br:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[CH2:15][OH:16]

Participants

6

Reactant 4

HCID 69402-Bromobenzoic acidHCID 8000Boron trifluoride etherateHCID 8058HexaneHCID 4311764Sodium borohydride

Product 1

HCID 728502-Bromobenzyl alcoholYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 5-liter, 3-necked glass reaction vessel equipped as described in Example 1 was charged with 62.4 grams (1.65 moles) of sodium borohydride, 1 liter of tetrahydrofuran, and 0.26 liter (2.1 moles) of boron trifluoride diethyl etherate at 0°-5°C using essentially the same procedure as described in Example 1. After stirring the reaction mixture for an additional 15 minutes, a solution of 400 grams (2 moles) of 2-bromobenzoic acid in 1 liter of tetrahydrofuran was added dropwise over a 1.5 hour period while maintaining a temperature of 0°-10°C. When the addition was complete, the reaction mixture was stirred for 6 hours at room temperature. Hydrolysis of the reaction mixture and recrystallization of the product from hexane gave 293 grams (78.5% yield) of 2-bromobenzyl alcohol as light-orange crystals, mp 78°-80°C.

Workup

  1. customA 5-liter, 3-necked glass reaction vessel
  2. customequipped
  3. temperaturewhile maintaining a temperature of 0°-10°C
  4. additionWhen the addition
  5. stirringthe reaction mixture was stirred for 6 hours at room temperature

Sources & evidence

ORD record
ord-d7bbd82a06c44839ac6d14d3c4c36cdf
Source dataset
uspto-grants-1976_08
Patent number
US03978140

Reaction notes

Loading…