Hydrogen Bromide → HCID 86750950, compound

HRID 1683432Notes

Reaction equation

HRID 1683432 reaction equation
Br.[F:2][C:3]([F:19])([CH2:14][C:15]([F:18])([F:17])[F:16])[C:4]([F:13])([F:12])[O:5][CH2:6][C:7]1([CH3:11])[CH2:10][O:9][CH2:8]1.[OH-:20].[Na+]>O>[F:19][C:3]([F:2])([CH2:14][C:15]([F:17])([F:18])[F:16])[C:4]([F:12])([F:13])[O:5][CH2:6][C:7]1([CH2:11][O:20][C:4]([F:12])([F:13])[C:3]([F:2])([F:19])[CH2:14][C:15]([F:16])([F:17])[F:18])[CH2:10][O:9][CH2:8]1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 86750951HCID 86750951, compound

Product 1

HCID 86750950HCID 86750950, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A 2-L, 3-neck, jacketed flask fitted with a mechanical stirrer, thermocouple probe, and an addition funnel was charged with 48% hydrobromic acid (208.0 g, 1.23 mole). The flask was cooled to 5° C. by circulating coolant through the jacket, and 3-heptafluorobutoxymethyl-3-methyloxetane was added at a rate to maintain the temperature below 12° C. The addition was complete after 11/4 hours. GC analysis indicated 98% conversion of the starting material to product. Additional 48% HBr (14.9 g, 0.088 mole) was added, and the mixture was stirred overnight at room temperature. The mixture was poured into 200-ml water, and the pH of the aqueous layer was adjusted to a pH of about 5 with 1N NaOH. The layers were separated, and the organic layer was washed with water (250 ml), dried (MgSO4), and filtered to give 300.4 g (93.5%) of 3-bromo-2-heptafluorobutoxymethyl-2-methyl-1-propanol (2), a clear oil: 1H NMR (CDCl3) 1.00 (s), 3.43 and 3.52 (AB, J=10.4 Hz), 3.53 and 3.59 (AB, J=11.1 Hz), 3.58 (s), and 3.95 (t, J=13.4 Hz); Anal. Calcd for C9H12BrF7O2 : C, 29.60; H, 3.32; Br, 21.88; Found: C, 29.15; H, 3.27; Br, 21.09.

Workup

  1. additionwas added at a rate
  2. temperatureto maintain the temperature below 12° C
  3. additionThe addition
  4. custom4 hours
  5. customThe layers were separated
  6. washthe organic layer was washed with water (250 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-644389de129c422e8308005046bbae60
Source dataset
uspto-grants-1997_06
Patent number
US05637772

Reaction notes

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